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** You can go karting with Eggman in ''VideoGame/SonicDrift'', and karting (more so airboarding) with Shadow in ''VideoGame/SonicRiders''
** In ''Sonic Drift 2'', you can not only kart with Eggman, but you can also choose Knuckles, Metal Sonic, and even Fang/Nack!
** And in ''VideoGame/SonicR'' it's not just Robotnik but four of his creations: Metal Sonic, Metal Knuckles, Tails Doll, and Egg Robo. The manual makes an attempt to say its a secret plot to destroy Sonic, but ingame all play fairly, and you can't destroy other racers.
** This has happened with Shadow in the games a few times too - though Shadow is more of TheRival than a villain, he and Sonic tend to be enemies most of the time (or at least, he really doesn't like Sonic). However, he teams up with Sonic or Tails in various levels in ''VideoGame/ShadowTheHedgehog'', races with the others in the various spin-off racing games, and appears at Sonic's birthday party in the ending to ''VideoGame/SonicGenerations''. He also shows up before the FinalBoss to give both Sonics some words of motivation, and gives them advice during the actual battle along with the other characters.

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** You can go karting with Eggman in ''VideoGame/SonicDrift'', and karting (more so airboarding) with Shadow in ''VideoGame/SonicRiders''
** In ''Sonic Drift 2'',
the second installment, you can not only kart with Eggman, but you can also choose Knuckles, Metal Sonic, and even Fang/Nack!
** And in ''VideoGame/SonicR'' it's not just In ''VideoGame/SonicR'', Robotnik but four of his creations: and Metal Sonic, Sonic come back alongside Metal Knuckles, Tails Doll, and Egg Robo. The manual makes an attempt to say its a secret plot to destroy Sonic, but ingame all play fairly, and you can't destroy other racers.
** While ''VideoGame/SonicTheFighters'' has a story mode where you must stop Robotnik to take over the world by collecting eight Emeralds and have to fight him after Metal Sonic, the multiplayer is a "Fighting with Eggman". The closest to this trope in a story playthrough is Fang who possesses one of the Emeralds, but is the only villain out of the eight base characters (contrary to popular belief, Bean and Bark are not allied with him).
** This has happened with Shadow in the games a few times too - though Shadow is more of TheRival than a villain, he and Sonic tend to be enemies most of the time (or at least, he really doesn't like Sonic). However, he teams up with Sonic or Tails in various levels in ''VideoGame/ShadowTheHedgehog'', races with the others in the various spin-off racing games, games like ''VideoGame/SonicRiders'', and appears at Sonic's birthday party in the ending to ''VideoGame/SonicGenerations''. He also shows up before the FinalBoss to give both Sonics some words of motivation, and gives them advice during the actual battle along with the other characters.



** The fangame ''VideoGame/SonicRoboBlast2Kart'' is essentially what could have happened if instead of ''Sonic R'', Creator/{{Sega}} decided to make a real ''VideoGame/MarioKart'' clone for the Platform/SegaSaturn: the base roster consists of Sonic , Tails and Knuckles, but also of [[BigBad Eggman]] and [[TheDragon Metal Sonic]], and the game includes an add-on with many other characters like Amy and [[BreakoutMookCharacter Motobug]], many other Classic, Dreamcast and Modern Eras protagonists and antagonists, [[MassiveMultiplayerCrossover and even other characters more or less affiliated to Sega since 1985]] ([[SerialEscalation and that's not even counting the mods]]). The sequel ''Dr. Robotnik's Ring Racers'' takes this trope even further, as Eggman and Tails allied to make go-karts that work with Rings and settled a championship where many protagonists and antagonists from the series participate (for starters, the base roster adds Mighty and Fang alongside the seven previously mentioned characters).

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** The fangame ''VideoGame/SonicRoboBlast2Kart'' is essentially what could have happened if instead of ''Sonic R'', Creator/{{Sega}} decided to make had made a real ''VideoGame/MarioKart'' clone for the Platform/SegaSaturn: Platform/SegaSaturn instead of ''Sonic R'': the base roster consists of Sonic , Sonic, Tails and Knuckles, but also of [[BigBad Eggman]] and [[TheDragon Metal Sonic]], and the game includes an add-on with many other characters like Amy and [[BreakoutMookCharacter Motobug]], many other Classic, Dreamcast and Modern Eras protagonists and antagonists, [[MassiveMultiplayerCrossover and even other characters more or less affiliated to Sega since 1985]] ([[SerialEscalation and that's not even counting the mods]]). The sequel ''Dr. Robotnik's Ring Racers'' takes this trope even further, as Eggman and Tails allied to make go-karts that work with Rings and settled a championship where many protagonists and antagonists from the series participate (for participate: for starters, the base roster adds Mighty and Fang alongside the seven previously mentioned characters).characters.
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** The fangame ''VideoGame/SonicRoboBlast2Kart'' is essentially what could have happened if instead of ''Sonic R'', Creator/{{Sega}} decided to make a real ''VideoGame/MarioKart'' clone for the Platform/SegaSaturn: the base roster consists of Sonic , Tails and Knuckles, but also of Eggman and Metal Sonic, and it includes an add-on with many other characters like Amy and [[BreakoutMookCharacter Motobug]], [[LoadsAndLoadsOfCharacters many other Classic, Dreamcast and Modern Eras protagonists and antagonists]], and even other characters more or less affiliated to Sega since 1985 (and that's not even counting the mods). The sequel ''Dr. Robotnik's Ring Racers'' takes this trope even further, as Eggman and Tails allied to make go-karts that work with Rings and settled a championship where many protagonists and antagonists from the series participate (for starters, the base roster adds Mighty and Fang alongside the seven previously mentioned characters).

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** The fangame ''VideoGame/SonicRoboBlast2Kart'' is essentially what could have happened if instead of ''Sonic R'', Creator/{{Sega}} decided to make a real ''VideoGame/MarioKart'' clone for the Platform/SegaSaturn: the base roster consists of Sonic , Tails and Knuckles, but also of Eggman [[BigBad Eggman]] and [[TheDragon Metal Sonic, Sonic]], and it the game includes an add-on with many other characters like Amy and [[BreakoutMookCharacter Motobug]], [[LoadsAndLoadsOfCharacters many other Classic, Dreamcast and Modern Eras protagonists and antagonists]], antagonists, [[MassiveMultiplayerCrossover and even other characters more or less affiliated to Sega since 1985 (and 1985]] ([[SerialEscalation and that's not even counting the mods).mods]]). The sequel ''Dr. Robotnik's Ring Racers'' takes this trope even further, as Eggman and Tails allied to make go-karts that work with Rings and settled a championship where many protagonists and antagonists from the series participate (for starters, the base roster adds Mighty and Fang alongside the seven previously mentioned characters).

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--->'''Shadow''': [[Creator/{{Egoraptor}} @egoraptor]] asks: "Sonic, have you and Tails just straight up forgotten how evil Robotnik is? I find it very disturbing to see y'all pal around with this joker!"
--->'''Sonic''': Y'know, it's a fair point that Eggman is pretty evil sometimes.
--->'''Tails''': And he has tried to ruin our lives on multiple occasions.
--->'''Shadow''': AND risked the lives of the entire planet.
--->'''Sonic''': But he's more like... a lovable kind of bad guy, y'know? There's just something about him. Well that, and he just shows up univited all the time.
--->'''Eggman''': Dear Arin Hanson, interesting question! I see you've chosen poorly when it comes to selecting your allies. I'll be in touch. VERY soon...
--->'''Sonic, Shadow, and Tails''': Dun DUN DUUUUUUUN!

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--->'''Shadow''': ---> '''Shadow''': [[Creator/{{Egoraptor}} @egoraptor]] asks: "Sonic, have you and Tails just straight up forgotten how evil Robotnik is? I find it very disturbing to see y'all pal around with this joker!"
--->'''Sonic''': ---> '''Sonic''': Y'know, it's a fair point that Eggman is pretty evil sometimes.
--->'''Tails''': ---> '''Tails''': And he has tried to ruin our lives on multiple occasions.
--->'''Shadow''': ---> '''Shadow''': AND risked the lives of the entire planet.
--->'''Sonic''': ---> '''Sonic''': But he's more like... a lovable kind of bad guy, y'know? There's just something about him. Well that, and he just shows up univited all the time.
--->'''Eggman''': ---> '''Eggman''': Dear Arin Hanson, interesting question! I see you've chosen poorly when it comes to selecting your allies. I'll be in touch. VERY soon...
--->'''Sonic, ---> '''Sonic, Shadow, and Tails''': Dun DUN DUUUUUUUN!DUUUUUUUN!
** The fangame ''VideoGame/SonicRoboBlast2Kart'' is essentially what could have happened if instead of ''Sonic R'', Creator/{{Sega}} decided to make a real ''VideoGame/MarioKart'' clone for the Platform/SegaSaturn: the base roster consists of Sonic , Tails and Knuckles, but also of Eggman and Metal Sonic, and it includes an add-on with many other characters like Amy and [[BreakoutMookCharacter Motobug]], [[LoadsAndLoadsOfCharacters many other Classic, Dreamcast and Modern Eras protagonists and antagonists]], and even other characters more or less affiliated to Sega since 1985 (and that's not even counting the mods). The sequel ''Dr. Robotnik's Ring Racers'' takes this trope even further, as Eggman and Tails allied to make go-karts that work with Rings and settled a championship where many protagonists and antagonists from the series participate (for starters, the base roster adds Mighty and Fang alongside the seven previously mentioned characters).
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* ''VideoGame/DisneySpeedstorm'': Disney villains [[WesternAnimation/MonstersInc1 Randall]], WesternAnimation/{{Pete}}, [[WesternAnimation/{{Aladdin}} Jafar]], [[WesternAnimation/{{Hercules}} Hades]], [[WesternAnimation/BeautyAndTheBeast Gaston]], [[WesternAnimation/LiloAndStitch Captain Gantu]], [[WesternAnimation/Frozen2013 Hans]], and [[WesternAnimation/TheLittleMermaid1989 Ursula]] are among the cast. Notably, the villains also drive for the same teams as their heroic adversaries.

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* ''VideoGame/DisneySpeedstorm'': Disney villains [[WesternAnimation/MonstersInc1 Randall]], WesternAnimation/{{Pete}}, [[WesternAnimation/{{Aladdin}} Jafar]], [[WesternAnimation/{{Hercules}} Hades]], [[WesternAnimation/BeautyAndTheBeast Gaston]], [[WesternAnimation/LiloAndStitch Captain Gantu]], [[WesternAnimation/Frozen2013 Hans]], and [[WesternAnimation/TheLittleMermaid1989 Ursula]] Ursula]], and [[WesternAnimation/WreckItRalph King Candy]] are among the cast. Notably, the villains also drive for the same teams as their heroic adversaries.
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* The NES game ''Eight Eyes'' shows your character having tea with a boss after defeating him/her.

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* The NES game ''Eight Eyes'' ''VideoGame/EightEyes'' shows your character having tea with a boss after defeating him/her.



* The ''Hoyle's Book of Games'' series, by [[Creator/{{Sierra}} Sierra Entertainment]], is a video game collection of card and later board games. In the first game, you could choose opponents from the heroes of various Sierra games. The Third game (the second was a collection of solitaire games so...) also allowed you to sit down and board games with various Sierra villains, such as [[VideoGame/SpaceQuest Sludge Vohaul]] and [[VideoGame/KingsQuest Mordack]]. They generally made villainous comments, though.

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* The ''Hoyle's Book of Games'' ''VideoGame/HoyleOfficialBookOfGames'' series, by [[Creator/{{Sierra}} Sierra Entertainment]], is a video game collection of card and later board games. In the first game, you could choose opponents from the heroes of various Sierra games. The Third game (the second was a collection of solitaire games so...) also allowed you to sit down and board games with various Sierra villains, such as [[VideoGame/SpaceQuest Sludge Vohaul]] and [[VideoGame/KingsQuest Mordack]]. They generally made villainous comments, though.



** Exploited by Chick Hicks in ''Cars Race-O-Rama''. If he wins the Race-O-Rama series, Radiator Springs will be under his control, Lightning and Mater will get kicked out, and Doc Hudson's Racing Academy will get shut down.

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** Exploited by Chick Hicks in ''Cars Race-O-Rama''.''VideoGame/CarsRaceORama''. If he wins the Race-O-Rama series, Radiator Springs will be under his control, Lightning and Mater will get kicked out, and Doc Hudson's Racing Academy will get shut down.



* ''Romancing [=SaGa=] [=Re:Universe=]''. During the New Year event, the Final Emperor from ''[[VideoGame/RomancingSaga2 Romancing [=SaGa=] 2]]'' is rather mystified by the fact he's assisting to a party along with his sworn enemies the Seven Heroes. In the end though, he comes around as he realizes they are not the same [[FallenHero fallen heroes]] bent on destroying mankind from his original world. Then the Emperor graciously accepts to share a drink with Subier and Rocbouquet.

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* ''Romancing [=SaGa=] [=Re:Universe=]''.''VideoGame/RomacingSaGaReUniverse''. During the New Year event, the Final Emperor from ''[[VideoGame/RomancingSaga2 Romancing [=SaGa=] 2]]'' is rather mystified by the fact he's assisting to a party along with his sworn enemies the Seven Heroes. In the end though, he comes around as he realizes they are not the same [[FallenHero fallen heroes]] bent on destroying mankind from his original world. Then the Emperor graciously accepts to share a drink with Subier and Rocbouquet.
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* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics. The games themselves are also a {{Meta}} example, due to the two franchises' [[UsefulNotes/The16BitEraOfConsoleVideoGames famous]] [[DuelingWorks rivalry]] in the 90's.

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* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics. The games themselves are also a {{Meta}} example, due to the two franchises' [[UsefulNotes/The16BitEraOfConsoleVideoGames [[MediaNotes/The16BitEraOfConsoleVideoGames famous]] [[DuelingWorks rivalry]] in the 90's.
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* ''VideoGame/DisneySpeedstorm'': Disney villains [[WesternAnimation/MonstersInc1 Randall]], WesternAnimation/{{Pete}}, [[WesternAnimation/{{Aladdin}} Jafar]], [[WesternAnimation/{{Hercules}} Hades]], [[WesternAnimation/BeautyAndTheBeast Gaston]], [[WesternAnimation/LiloAndStitch Captain Gantu]], and [[WesternAnimation/Frozen2013 Hans]] are among the cast. Notably, the villains also drive for the same teams as their heroic adversaries.

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* ''VideoGame/DisneySpeedstorm'': Disney villains [[WesternAnimation/MonstersInc1 Randall]], WesternAnimation/{{Pete}}, [[WesternAnimation/{{Aladdin}} Jafar]], [[WesternAnimation/{{Hercules}} Hades]], [[WesternAnimation/BeautyAndTheBeast Gaston]], [[WesternAnimation/LiloAndStitch Captain Gantu]], and [[WesternAnimation/Frozen2013 Hans]] Hans]], and [[WesternAnimation/TheLittleMermaid1989 Ursula]] are among the cast. Notably, the villains also drive for the same teams as their heroic adversaries.
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* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics. To say nothing about both franchises themselves and [[UsefulNotes/The16BitEraOfConsoleVideoGames their]] [[DuelingWorks famous rivalry]] in the 90's.

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* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics. To say nothing about both franchises The games themselves and are also a {{Meta}} example, due to the two franchises' [[UsefulNotes/The16BitEraOfConsoleVideoGames their]] famous]] [[DuelingWorks famous rivalry]] in the 90's.
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* ''VideoGame/LooneyTunesBBall'' has Bugs Bunny playing a game of basketball against several members of his RoguesGallery; Daffy Duck, Elmer Fudd, Yosemite Sam, Wile E. Coyote, Taz, and Marvin the Martian. Sylvester is the notable exception, since while he is still often portrayed as an antagonist in the Looney Tunes universe, Bugs isn't one of his targets.

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* ''VideoGame/LooneyTunesBBall'' has Bugs Bunny playing a game of basketball against several members of his RoguesGallery; Daffy Duck, Elmer Fudd, Yosemite Sam, Wile E. Coyote, Taz, and Marvin the Martian. Sylvester is the notable exception, since while he is still often portrayed as an antagonist in the Looney Tunes universe, Bugs isn't one of his targets.targets.
* ''VideoGame/DisneySpeedstorm'': Disney villains [[WesternAnimation/MonstersInc1 Randall]], WesternAnimation/{{Pete}}, [[WesternAnimation/{{Aladdin}} Jafar]], [[WesternAnimation/{{Hercules}} Hades]], [[WesternAnimation/BeautyAndTheBeast Gaston]], [[WesternAnimation/LiloAndStitch Captain Gantu]], and [[WesternAnimation/Frozen2013 Hans]] are among the cast. Notably, the villains also drive for the same teams as their heroic adversaries.
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--->'''Shadow''': [[Creator/Egoraptor @egoraptor]] asks: "Sonic, have you and Tails just straight up forgotten how evil Robotnik is? I find it very disturbing to see y'all pal around with this joker!"

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--->'''Shadow''': [[Creator/Egoraptor [[Creator/{{Egoraptor}} @egoraptor]] asks: "Sonic, have you and Tails just straight up forgotten how evil Robotnik is? I find it very disturbing to see y'all pal around with this joker!"
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** It was discussed in [[Blog/SonicTheHedgehogTwitter Sonic Twitter Takeover 4]].
--->'''Shadow''': [[Creator/Egoraptor @egoraptor]] asks: "Sonic, have you and Tails just straight up forgotten how evil Robotnik is? I find it very disturbing to see y'all pal around with this joker!"
--->'''Sonic''': Y'know, it's a fair point that Eggman is pretty evil sometimes.
--->'''Tails''': And he has tried to ruin our lives on multiple occasions.
--->'''Shadow''': AND risked the lives of the entire planet.
--->'''Sonic''': But he's more like... a lovable kind of bad guy, y'know? There's just something about him. Well that, and he just shows up univited all the time.
--->'''Eggman''': Dear Arin Hanson, interesting question! I see you've chosen poorly when it comes to selecting your allies. I'll be in touch. VERY soon...
--->'''Sonic, Shadow, and Tails''': Dun DUN DUUUUUUUN!
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Killer 7


* Harman and Kun Lan in ''VideoGame/{{Killer7}}''. Necessary because they're both immortal; since neither can have ultimate victory, they have to settle for getting best two out of three at chess. Or global thermonuclear war. Whichever strikes their fancy.

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* Harman and Kun Lan in ''VideoGame/{{Killer7}}''. Necessary because they're both immortal; since neither can have ultimate victory, they have to settle for getting best two out beating each other at chess, international terrorism, the destruction of three at chess. Or global thermonuclear war. Whichever nations...whichever strikes their fancy.
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** In ''Kirby's Dream Collection'', [[spoiler:Magolor is back after [[HeelFaceTurn having atoned for his sins]] (as seen in the Magolor Epilogue in ''VideoGame/KirbysReturnToDreamLandDeluxe''), and you could even do some friendly races with him.]]. He continues to be friendly in his shopkeeper role in ''VideoGame/TeamKirbyClashDeluxe''. [[spoiler:Looks like not even final bosses stay consistently evil, [[JustifiedTrope ''especially'' after a trip to Another Dimension and a battle with the very object of their ambition...]]]]

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** In ''Kirby's Dream Collection'', [[spoiler:Magolor is back after [[HeelFaceTurn having atoned for his sins]] (as seen in the Magolor Epilogue in ''VideoGame/KirbysReturnToDreamLandDeluxe''), and you could even do some friendly races with him.]]. He continues to be friendly in his shopkeeper role in ''VideoGame/TeamKirbyClashDeluxe''. [[spoiler:Looks like not even final bosses stay consistently evil, [[JustifiedTrope ''especially'' especially after a trip to Another Dimension and a battle with the very object of their ambition...]]]]
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** In ''Kirby's Dream Collection'', [[spoiler:Magolor is back and [[HeelFaceTurn seems to have reformed]]. You could even do some friendly races with him. Not even the final bosses are consistently evil]]. He continues to be friendly in his shopkeeper role in ''VideoGame/TeamKirbyClashDeluxe''.

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** In ''Kirby's Dream Collection'', [[spoiler:Magolor is back and after [[HeelFaceTurn seems to have reformed]]. You having atoned for his sins]] (as seen in the Magolor Epilogue in ''VideoGame/KirbysReturnToDreamLandDeluxe''), and you could even do some friendly races with him. Not even the final bosses are consistently evil]].him.]]. He continues to be friendly in his shopkeeper role in ''VideoGame/TeamKirbyClashDeluxe''. [[spoiler:Looks like not even final bosses stay consistently evil, [[JustifiedTrope ''especially'' after a trip to Another Dimension and a battle with the very object of their ambition...]]]]
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Crosswicking

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** Unlike most other ''VideoGame/MarioParty'' games where Bowser spends his time bullying the players, in ''VideoGame/SuperMarioParty'' he and his minions join the games on equal grounds with the other playable characters.
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* VideoGame/LooneyTunesBBall has Bugs Bunny playing a game of basketball against several members of his RoguesGallery; Daffy Duck, Elmer Fudd, Yosemite Sam, Wile E. Coyote, Taz, and Marvin the Martian. Sylvester is the notable exception, since while he is still often portrayed as an antagonist in the Looney Tunes universe, Bugs isn't one of his targets.

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* VideoGame/LooneyTunesBBall ''VideoGame/LooneyTunesBBall'' has Bugs Bunny playing a game of basketball against several members of his RoguesGallery; Daffy Duck, Elmer Fudd, Yosemite Sam, Wile E. Coyote, Taz, and Marvin the Martian. Sylvester is the notable exception, since while he is still often portrayed as an antagonist in the Looney Tunes universe, Bugs isn't one of his targets.
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* The game ''Series/PowerRangersZeo: Battle Racers'' has [[BigBad King Mondo]] and a [[{{Mook}} Cog]] casually racing with the Rangers.

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* The game ''Series/PowerRangersZeo: Battle Racers'' has [[BigBad King Mondo]] and a [[{{Mook}} Cog]] casually racing with the Rangers.Rangers.
* VideoGame/LooneyTunesBBall has Bugs Bunny playing a game of basketball against several members of his RoguesGallery; Daffy Duck, Elmer Fudd, Yosemite Sam, Wile E. Coyote, Taz, and Marvin the Martian. Sylvester is the notable exception, since while he is still often portrayed as an antagonist in the Looney Tunes universe, Bugs isn't one of his targets.
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** The main gist of Gourmet Race in ''Super Star'' is that Kirby and [[TheRival King Dedede]] have a friendly competition to see who can eat the most food.
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* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics.

to:

* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics. To say nothing about both franchises themselves and [[UsefulNotes/The16BitEraOfConsoleVideoGames their]] [[DuelingWorks famous rivalry]] in the 90's.
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* ''VideoGame/SonicTheHedgehog'':

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* ''VideoGame/SonicTheHedgehog'':''Franchise/SonicTheHedgehog'':
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* ''Videogame/{{Littlewood}}'' has this in a purely technical sense, between an AmnesiacHero and an AmnesiacVillainJoinsTheHeroes who don't even remember ever being enemies.

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* ''Videogame/{{Littlewood}}'' has this in a purely technical sense, between an AmnesiacHero and an AmnesiacVillainJoinsTheHeroes who don't even remember ever being enemies.enemies.
* The game ''Series/PowerRangersZeo: Battle Racers'' has [[BigBad King Mondo]] and a [[{{Mook}} Cog]] casually racing with the Rangers.
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* ''VideoGame/NickelodeonKartRacers 2'', in addition to Angelica and Zim above, also has [[Franchise/TeenageMutantNinjaTurtles Oroku Saki, aka the Shredder]], the Teenage Mutant Ninja Turtles' ArchEnemy who is usually portrayed as one of the Turtles' more dangerous antagonists (taken further since the turtles use their [[WesternAnimation/TeenageMutantNinjaTurtles2012 2012 designs]], and 2012 Shredder is second only to [[WesternAnimation/TeenageMutantNinjaTurtles2003 Utrom Shredder]] in terms of evil).
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* Practically every ending of every installment of ''Franchise/TouhouProject'' have the main characters sit down and drink tea with the last boss after they save the world from the said last boss. Most of the villains are just Youkai who get it into their head to do something destructive. In fact, Go Karting With Bowser is the ''entire idea'' behind Mountain of Faith's Extra stage.

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* Practically every ending of every installment of ''Franchise/TouhouProject'' have the main characters sit down and drink tea alcohol with the last boss after they save the world from the said last boss. Most of the villains are just Youkai who get it into their head to do something destructive. In fact, Go Karting With Bowser is the ''entire idea'' behind Mountain of Faith's Extra stage.
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* ''Franchise/SuperMarioBros'':
** The [[TropeNamers classic example of this trope]] is King Koopa himself, Bowser. He is a notorious warlord and chronic princess-kidnapper in the main-series and RPG games, but in ''VideoGame/MarioKart'' series and [[VideoGame/MarioTennis many]], [[VideoGame/MarioGolf many]] [[VideoGame/MarioStrikers sports]] [[VideoGame/MarioSuperSluggers game]] [[VideoGame/MarioSportsMix spinoffs]] Mario and Peach have no problem challenging him to some friendly competition. Bowser Jr., the Koopalings and several Koopa Troop members also join in the fun.
--->'''Cracked:''' ''[[http://www.cracked.com/article_18863_5-reasons-bowser-most-successful-video-game-character.html#ixzz1Or3e8U8R Repeated home invasions and sexual assaults normally lead to restraining orders, not golf invitations.]]''
** In ''VideoGame/MarioKartDoubleDash'', you can take this trope [[ExactWords word for word]] by pairing them in a single kart.
** Best exemplified in the intro to ''[[VideoGame/MarioTennis Mario Tennis 64]]''. Bowser and Boo barge into the tournament via their sinister battleship and confront Mario and Luigi, before cheerfully requesting a match.
--->'''Mario:''' Hey, let's-a ALL play!
** Mario explains his logic in [[https://www.engadget.com/2011/02/07/mario-sports-mix-press-conference-reveals-marios-dreams-and-a/ this interview]]:
---> '''Mario:''' Well, you know what dey say, [[Film/TheGodfather keep you friends-a close, and you enemies-a closer]]. But dey also say, if you enemy is a gigantic spiky creature, who breathes-a da fire, keep him-a super-duper close!
** EvilCounterpart / TheRival Wario has been go-karting and playing sports since ''VideoGame/MarioKart64'' and Waluigi has been by his side since his introduction in ''[[VideoGame/MarioTennis Mario Tennis 64]]''.
** WordOfGod explains the relationship of Mario characters to be much like [[AnimatedActors "actors" from a cartoon show]].
--->'''[[http://www.gameinformer.com/b/features/archive/2012/09/24/miyamoto-tezuka-interview.aspx Shigeru Miyamoto]]:''' If you're familiar with things like ComicStrip/{{Popeye}} and some of the old comic characters, you would oftentimes see this cast of characters that takes on [[UniversalAdaptorCast different roles depending on the comic or cartoon]]. They might be businessman in one [cartoon] or a pirate in another. Depending on the story that was being told, they would change roles. So, to a certain degree, I look at our characters in a similar way and feel that they can take on different roles in different games. It's more like they're one big family, or maybe a troupe of actors.
* ''VideoGame/JadeEmpire'' has two representatives of the Way of the Open Palm and the Way of the Closed Fist (the [[LawfulStupidChaoticStupid game's rough way]] of saying "Good" and "Evil") meet once a year to play a game vaguely reminiscent of go. Without any pieces. ''Or a BOARD.'' Once you've chosen one philosophy for your own and learn the corresponding martial art, the two conclude their game and vow to meet up next year... if something bad doesn't happen in the time in-between.
* Harman and Kun Lan in ''VideoGame/{{Killer7}}''. Necessary because they're both immortal; since neither can have ultimate victory, they have to settle for getting best two out of three at chess. Or global thermonuclear war. Whichever strikes their fancy.
* In ''VideoGame/TheSims2'', anyone whom you're furious with or enemies with can be invited to a wedding. And they'll come. ''And share cake, toast to you and even clap for you when it's over.'' But next time you see them, they're back to fighting you.
* In ''VideoGame/FinalFantasyVI'', after having spent half the game chasing Terra, having sentenced Celes ([[HeelFaceTurn a former General in their army]]) to death, occupied Edgar and Sabin's kingdom, [[ThrowAwayCountry destroyed Doma]], [[MagiTek killed countless Espers]], and basically waging war against the entire world (a war which he was close to winning), Emperor Gestahl invites the heroes to a nice and civilized diplomatic dinner, just to show he's not a bad guy anymore. (He still is. The whole thing was a ruse.)\\\
It's worth noting he blamed Kefka for almost everything, even going as far as asking the party what should they do with said AxCrazy[=/=][[TheCaligula Caligula]]/[[StrawNihilist Nietzsche Wannabe]][=/=]OmnicidalManiac, [[JustForFun/TropeOverdosed trope overdose]] etc. One of the options is to execute him, though the correct choice (in terms of in-game rewards) is to leave him in jail. It's also worth mentioning that [[spoiler:the cast didn't fall for the ruse and tried to plan for an eventual betrayal. They just didn't realize the actual evil plan in time for it to be prevented]].
* ''VideoGame/FinalFantasyXV'' has a short section where you Drive in a Convoy with [[BigBad Ardyn]].
* ''Franchise/{{Kirby}}'' games do this a lot:
** Kirby can choose to use his Copy Ability to make a "helper" (for example, Fighter Kirby summons Knuckle Joe), who are friendly versions of the enemies swallowed.
** Chef Kawasaki is a [[MiniBoss mid-boss]] in ''VideoGame/KirbySuperStar'', but otherwise appears in friendlier roles outside of the spinoffs. In ''VideoGame/KirbysDreamLand3'', he challenges Kirby to a friendly game that can earn him a reward. In ''Anime/KirbyRightBackAtYa'', he gives Kirby a (short-lived) job at his restaurant.
** In ''Kirby's Dream Collection'', [[spoiler:Magolor is back and [[HeelFaceTurn seems to have reformed]]. You could even do some friendly races with him. Not even the final bosses are consistently evil]]. He continues to be friendly in his shopkeeper role in ''VideoGame/TeamKirbyClashDeluxe''.
** This is taken to its logical conclusion in ''VideoGame/KirbyStarAllies'', where more villains like Marx, Dark Meta Knight, and even the Mage Sisters find themselves teaming up with Kirby to save the universe.
** Inverted with King Dedede who tends to [[RivalsTeamUp team up with Kirby]] against a greater threat in the main games, but usually plays the BigBad in the spinoffs like ''Kirby's Super Star Stacker'', and ''Kirby Tilt 'n' Tumble''.
* Judging by the way the original developers handled the franchise, ''VideoGame/CrashBandicoot'' seems to have a bit of this going on with [[MadScientist Dr. Neo Cortex]] and several other villains, specifically in ''VideoGame/CrashTeamRacing'' where the good guys and bad guys are all just go-karting along even before the plot happens... and then they all go-kart around some more to [[SavingTheWorld save the world]] from an alien who will turn it into a parking lot if they can't beat him in a race.
* Practically every ending of every installment of ''Franchise/TouhouProject'' have the main characters sit down and drink tea with the last boss after they save the world from the said last boss. Most of the villains are just Youkai who get it into their head to do something destructive. In fact, Go Karting With Bowser is the ''entire idea'' behind Mountain of Faith's Extra stage.
* The NES game ''Eight Eyes'' shows your character having tea with a boss after defeating him/her.
* ''VideoGame/DeadOrAlive Xtreme Beach Volleyball''. Characters that would otherwise be at each other's throats just want to relax at the beach. Even characters like Ayane/Kasumi, Helena/Ayane, and Christie/Helena, who all have a kill on sight method of greeting each other in canon have only a small grudge. Justified though, as it's AllJustADream by Zack.
* There's an old Namco platforming game for the Sega Genesis called ''[[VideoGame/MarvelLand Talmit's Adventure]]'', where the leading character, Talmit, had to beat 3 of [[BigBad the Mole King's]] underlings to save three fairies and their princess trapped in magical orbs, complete with SmoochOfVictory. Nothing wrong with that, until you realize that every single boss battle is a Mini-game with lots of TheComputerIsACheatingBastard. The minigames, themselves prove to be quite entertaining though, even, surprisingly, the Rock Paper Scissors battle with a twist. After beating the last world, you are pitted against the Mole King who plays a variation of Whack-a-Mole against you. The ridiculousness of this is even taken in account by the Big Bad himself, who after losing attacks you and becomes the first and last real boss of the game.
* Done quite literally in ''VideoGame/GrandTheftAutoSanAndreas''. The protagonist, CJ kills his way through rapper Madd Dogg's mansion to steal his rhyme book so a friend, OG Loc, can jumpstart his music career. After [[TheAtoner saving]] Madd Dogg from a suicide attempt, CJ chases OG Loc through the streets of Los Santos in go karts, in order to get the rhyme book back to its rightful owner.
* In ''VideoGame/CityOfHeroes'', the heroes and villains can fight over an island in Bloody Bay or Warburg, protect/invade [[CityOfAdventure Paragon City]] in Siren's Call, or fight over the future in Recluse's Victory. Alternatively, they can have a drink and go on a few missions together in the Pocket D dance club, work to protect the past in [[AncientRome Cimerora]] and the Midnighter's Club, and fight aliens in the Rikti War Zone.
* ''VideoGame/SonicTheHedgehog'':
** You can go karting with Eggman in ''VideoGame/SonicDrift'', and karting (more so airboarding) with Shadow in ''VideoGame/SonicRiders''
** In ''Sonic Drift 2'', you can not only kart with Eggman, but you can also choose Knuckles, Metal Sonic, and even Fang/Nack!
** And in ''VideoGame/SonicR'' it's not just Robotnik but four of his creations: Metal Sonic, Metal Knuckles, Tails Doll, and Egg Robo. The manual makes an attempt to say its a secret plot to destroy Sonic, but ingame all play fairly, and you can't destroy other racers.
** This has happened with Shadow in the games a few times too - though Shadow is more of TheRival than a villain, he and Sonic tend to be enemies most of the time (or at least, he really doesn't like Sonic). However, he teams up with Sonic or Tails in various levels in ''VideoGame/ShadowTheHedgehog'', races with the others in the various spin-off racing games, and appears at Sonic's birthday party in the ending to ''VideoGame/SonicGenerations''. He also shows up before the FinalBoss to give both Sonics some words of motivation, and gives them advice during the actual battle along with the other characters.
** In the two-player mode of ''VideoGame/SonicAdventure2'', Sonic can have a friendly race with Shadow and Metal Sonic. He can also actually go go-karting with Shadow (but not with Metal Sonic, since he's not selectable in that mode). Even more, Amy can also race against Metal Sonic, despite the fact she should have every reason to hate him given that he's the one who kidnapped her back in ''VideoGame/SonicTheHedgehogCD''.
** In ''[[VideoGame/SegaSuperstars Sonic & Sega All Stars Racing]]'', of course, Sonic is seeing karting with Eggman and Shadow. Shadow's profile actually reminds you of his CharacterDevelopment from revenge-driven maniac to TheLancer.
** Creator/{{Sega}} themselves [[LampshadeHanging lampshaded]] this during the second annual Sonic Website/{{Twitter}} takeover (itself an example of this trope, with Sonic and Eggman answering fan-tweeted questions together). Creator/{{Sega}} asked them "Do you guys hang out a lot or are you actually {{fr|iendlyEnemy}}enemies?" Eggman's response is to [[SuspiciouslySpecificDenial loudly and emphatically declare "We're ''enemies''! MORTAL enemies!"]], then [[IResembleThatRemark offer to get Sonic a leftover]] [[TrademarkFavoriteFood chili dog]] [[IResembleThatRemark from the fridge.]]
** The third Sonic Website/{{Twitter}} had [[TheRival Shadow]] answering questions along with Sonic and Eggman.
* ''VideoGame/MarioAndSonicAtTheOlympicGames'' features both Bowser and Robotnik/Eggman (as well as many of their associates such as Bowser Jr., Metal Sonic, and certain members of the Koopalings and Deadly Six) participating fairly in the Olympics.
* ''VideoGame/KonamiKrazyRacers'' allows you to play as Dracula himself, ''Franchise/{{Castlevania}}'' music and race tracks included. The sequel ''Krazy Kart Racing'' added [[Franchise/SilentHill Pyramid Head]] as a new racer.
* In one of the endings of ''VideoGame/TheBardsTale'', [[spoiler:The Bard, rather than side with either the demonic princess or the Druids trying to seal her away, tells them both to "sod off" and heads to the nearest tavern. The ending shows him hanging out in the tavern with the undead {{mooks}} he's been fighting throughout the game, who actually aren't that bad once you get to know them]].
* The ''Hoyle's Book of Games'' series, by [[Creator/{{Sierra}} Sierra Entertainment]], is a video game collection of card and later board games. In the first game, you could choose opponents from the heroes of various Sierra games. The Third game (the second was a collection of solitaire games so...) also allowed you to sit down and board games with various Sierra villains, such as [[VideoGame/SpaceQuest Sludge Vohaul]] and [[VideoGame/KingsQuest Mordack]]. They generally made villainous comments, though.
* In ''VideoGame/DonkeyKong64'', [[spoiler:the 100% completion bonus scene shows the characters as actors. Donkey Kong and K. Rool are seen playing patty-cake]].
* ''VideoGame/RaymanM'' (known as ''[[MarketBasedTitle Rayman Arena]]'' in the US) has Rayman and his friends and enemies engage in a racing competition, although the canonicity thereof is uncertain. (They can still beat each other up in the battle segments, though.)
* The Creator/{{Nickelodeon}} party game ''VideoGame/NickelodeonPartyBlast'' features several iconic Franchise/{{Nicktoons}} heroes in its playable lineup, such as [[WesternAnimation/{{Rugrats}} Tommy Pickles]], WesternAnimation/SpongeBobSquarePants and [[WesternAnimation/TheAdventuresOfJimmyNeutronBoyGenius Jimmy Neutron]]. While most of these characters are straight-up heroes, the roster also includes [[WesternAnimation/{{Rugrats}} Angelica Pickles]], a selfish brat who often comes into conflict with the other main babies in her home series, and WesternAnimation/InvaderZim, who happens to be a VillainProtagonist who wants to [[TakeOverTheWorld take over Earth]] in his home series.
* In ''VideoGame/NicktoonsMLB'', you can play baseball with [[WesternAnimation/InvaderZim Zim]] and '''[[WesternAnimation/SpongebobSquarepants The Flying Dutchman!]]'''
* ''VideoGame/HeavyRain'' has this with a golf match between Scott Shelby and Charles Kramer.
* Played straight in ''VideoGame/KingdomHeartsBirthBySleep'', with the Rumble Racing minigame, as well as some of the Command Boards. You play against Gantu, Captain Hook, Maleficent...
* ''VideoGame/PokemonBlack2AndWhite2'' has Giovanni, the BigBad of the first two games and the main villain of the anime, in the Pokémon World Tournament, due to his old position as Viridian City Gym Leader.
* During a Space Route scenario in ''VideoGame/ShinSuperRobotWars'', Hathaway Noa is chatting with Quess Pariya, who wants to know what Amuro is like. Hathaway, confused, says that Amuro is totally normal. Quess says that she's studying yoga, hoping to gain the ability to know what people are like even without talking to them - much like the fabled Newtypes can.
* ''VideoGame/AngryBirdsGo'': The only time the birds and pigs aren't feuding with each other. Case in point, they're racing for a cake.
* Crow, the [[VillainProtagonist supervillain main character]] of ''{{VideoGame/Nefarious}}'', frequently gets invited over to go-kart races by Princess Mayapple, despite routinely kidnapping her and trying to take over her kingdom.
* Invoked in ''VideoGame/MortalKombatX'' with Cassie Cage's "Selfie" Fatality, where she breaks off her victim's jaw, snaps a selfie, and uploads it to her social media account. The other kombatants may post comments about her pic, including characters like Mileena or Quan Chi. This is lampshaded whenever Kano makes a comment and Sonya will ask "Cassie, why is Kano on your friends list?"
** ''Videogame/MortalKombat11'' has this in Kitana's Friendship, where Mileena, her evil cannibal clone who wants her dead more than anything, shows up so both can play patty-cake like actual sisters.
** For a more literal of the trope, ''Videogame/MortalKombatArmageddon'' has the RacingMinigame "Motor Kombat".
* In the ''Franchise/{{Pokemon}}'' universe, it's said that the Zangoose and Seviper species are mortal enemies so vicious, their hatred is hardwired into their ''genetics''. You can make a Zangoose and a Seviper breed.
* In ''VideoGame/PuyoPuyo'', everyone can play a match with the likes of {{Satan}} and [[EldritchAbomination Ecolo]], just for fun.
* In ''Videogame/AsurasWrath'', Augus is sent by the Seven Deities to kill Asura, his former pupil. When he finds him, he insists that the two bathe together in a hot spring, and enjoy drinks and the company of several beautiful women, before their epic duel to the death.
* ''VideoGame/TheLegendOfZeldaBreathOfTheWild'' allows Link to [[https://www.youtube.com/watch?v=sfYxssXyOyk&list=PLSQLREUw9vwlh8bzgvZCt_WS8615trN5H&index=4&t=17s hang out with various monsters]] by wearing disguises.
* ''VideoGame/ShrekSmashNCrashRacing'' features [[PrinceCharmless Prince Charming]] and [[TortureTechnician Thelonious]] as playable racers alongside ''{{Franchise/Shrek}}'' regulars like Shrek himself, Donkey and Fiona.
* In ''VideoGame/TheSecretWorld'', the mission "Dead Man's Hand" features an occasional poker game between bigwigs from the three main opposing factions: [[KnightTemplar Templar]] [[ReasonableAuthorityFigure administrator]] [[QuintessentialBritishGentleman Richard Sonnac]], [[TheIlluminati Illuminati]] [[MeanBoss handler]] [[FairWeatherMentor Kirsten Geary]] and [[TheChessmaster Dragon]] [[TheConsigliere majordomo]] [[SuccessThroughInsanity Daimon Kiyota]] all meet up in order to exchange banter and gamble for information on relatively peaceful terms. For good measure, the mission involves [[{{Mummy}} Saïd]] of [[TheNecrocracy the Kingdom]] getting involved as well...
* ''VideoGame/SuperSmashBrosUltimate'': In the trailer in which [[VideoGame/BanjoKazooie Banjo and Kazooie]] are revealed, King K. Rool, the BigBad of the ''Donkey Kong'' franchise, is shown casually hanging out with Donkey Kong and Diddy Kong.
* The Story Mode of ''VideoGame/{{Cars}}'' has a few events where Lightning [=McQueen=] casually races against Chick Hicks, the Delinquent Road Hazards and the Queens Gang outside of any racing series. [[JustifiedTrope Justified]], as their rivalry involves only racing [[spoiler: for the most part]].
** In ''VideoGame/CarsMaterNationalChampionship'' Snot Rod, the Queens Gang and the Monster Trucks return for a friendly competition.
** Exploited by Chick Hicks in ''Cars Race-O-Rama''. If he wins the Race-O-Rama series, Radiator Springs will be under his control, Lightning and Mater will get kicked out, and Doc Hudson's Racing Academy will get shut down.
** In ''Cars 2'', however, you can have a friendly no-weapons race with some of the Lemons, plus Delinquent Road Hazards if you have DLC installed. [[JustifiedTrope Justified]] yet again, since the entire game is just a simulation.
** The story mode of ''VideoGame/Cars3DrivenToWin'' yet again takes place in a simulation, however, it's all part of a "Lightning Storm Cruise" event, so Miss Fritter, Chick Hicks and Jackson Storm aren't here for a friendly race. However, Chick invites Lightning [=McQueen=] and some of his friends to his talk show, and in the end the two rivals [[spoiler:share a laugh watching Storm get chased by Fritter]].
* In ''[[VideoGame/{{Yakuza1}} Yakuza Kiwami]]'', a remake of the first ''Yakuza'' game, the [[CharacterizationMarchesOn at-the-time-minor-villain]] Goro Majima is given a vastly expanded role in which he constantly stalks Kiryu and tries to goad him into a fight. While most of the time this just means physically fighting him, in some situations you'll end up bowling, throwing darts, playing pool, racing slot-cars, or even ''[[DisguisedInDrag dating him]]'' instead. This would only be out-of-the-ordinary (for Majima) if this wasn't a remake of the one game in which he's actually a villain and does things like kidnap a little girl and drive a truck into a building.
* ''VideoGame/MarioSuperSluggers'' features Bowser, King Boo and [[VideoGame/DonkeyKongCountry King K. Rool]] all competing with their nemeses in the friendly pastime of baseball. [[spoiler:Although Bowser ''does'' try to take over the Baseball Kingdom via his son Junior, in the story mode.]]
* ''VideoGame/TheNeverhood'': The Japan-only GaidenGame ''Klaymen Gun Hockey'' involves the BigBad Klogg returning to the Neverhood to challenge the cast to a game of air hockey played with guns.
* Gruntilda appears in ''VideoGame/BanjoPilot'', an airplane racing game based on ''VideoGame/BanjoKazooie'' as one of the game's playable racers, but she poses no real threat to Banjo, Kazooie, and the rest of their friends.
* ''VideoGame/{{Deltarune}}'': While on the lookout for the missing Noelle, the {{Big Bad}} of the chapter, Queen, decides to call "trucies" with Kris and later begins to feel particularly exhausted with [[BumblingSidekick Berdly]] and her own issues and conflicts. To let out some steam, she offers to play the arcade game she previously used to attempt to destroy their confidence with them just for fun. It all seems to be going well until [[MomentKiller Berdly appears with a giant buffed up statue of himself, crushing the arcade machine in the process]].
* ''Romancing [=SaGa=] [=Re:Universe=]''. During the New Year event, the Final Emperor from ''[[VideoGame/RomancingSaga2 Romancing [=SaGa=] 2]]'' is rather mystified by the fact he's assisting to a party along with his sworn enemies the Seven Heroes. In the end though, he comes around as he realizes they are not the same [[FallenHero fallen heroes]] bent on destroying mankind from his original world. Then the Emperor graciously accepts to share a drink with Subier and Rocbouquet.
* ''VideoGame/{{Madagascar}}'': The Shuffleboarding minigame allows Alex, Marty, Gloria and Melman to play with Big Louie, Crocky and the Foosa King, all of whom are enemies fought throughout the game.
* ''Videogame/{{Littlewood}}'' has this in a purely technical sense, between an AmnesiacHero and an AmnesiacVillainJoinsTheHeroes who don't even remember ever being enemies.

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