Basic Trope: A boss character who is fought multiple times.
- Straight: Ray Curring fights Bob numerous times throughout the game.
- Exaggerated: Every single boss fight is against Ray.
- Downplayed: Ray is only fought twice, and he has a heart attack in the middle of the second fight, cutting it short.
- Justified:
- Ray is the Big Bad's only minion who isn't a mere mook, so he ends up relying on him to keep Bob at bay numerous times.
- Ray's very determined to beat Bob, so he keeps challenging Bob to rematches, trying to best him.
- Bob keeps interrupting Ray's operations, who always abandons ship when his HP is at or below 10% to heal and plan another heist, until the encounter in the last level, where he has wised up and turns himself in to the police the moment he sees Bob.
- Inverted: Ray is The Unfought.
- Subverted: Just when it looks like Ray will be fought a second time, he gets eaten by a giant monster. The monster is the real boss.
- Double Subverted: The monster eats Bob as well, and he ends up fighting Ray inside the monster's stomach.
- Parodied: Ray is fought at the end of every level, and anytime a different boss shows up, it turns out to be Ray in disguise, including the Final Boss.
- Zig Zagged: The Ray fought inside the monster is Actually a Doombot. Not only that, but the first encounter with Ray is later revealed to have been his twin brother, not Ray himself. The real Ray turns out be Dragon Their Feet after the battle with the Big Bad.
- Averted: No boss is fought more than once.
- Enforced: The developers ran out of time, so they were forced to scrap two previously planned boss fights and replace them with rematches against Ray.
- Lampshaded: "How many times do I have to fight this guy before he gives up?"
- Invoked: Ray undergoes a ritual that allows him to reincarnate himself infinitely and keep rematching Bob no matter how many times he dies fighting him.
- Exploited: Bob remembered his first fight with Ray and memorized his attack patterns, knowing he would have to fight him again. Ray goes down rather easily the second time because of this.
- Defied: Ray shows up for a rematch, but Bob refuses to fight him a second time, declaring that it isn't worth his time to fight him again. Instead, he swipes the Plot Coupon, escapes the building, and blows it up, killing Ray.
- Discussed: "I've played enough video games to know that I'll end up having to fight Ray again."
- Conversed: "You know those video game bosses that show up multiple times, and you have to keep fighting them?"
- Implied: A monster fought later on is heavily implied, though not outright stated, to be a One-Winged Angel form of Ray.
- Played For Laughs:
- Goldfish Poop Gang
- Bob starts making bets on when Ray will show up again.
- Played For Drama: Ray is an Implacable Man, and the game is a feeble attempt by Bob to finish off the evil that has been stalking him for years.
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