History Main / AgingWouldBeHipster

* ''Series/ModernFamily'': Phil Dunphy tries to be the "cool" dad to his three kids by staying hip to modern pop culture. He doesn't do very well -- he thinks WTF means "why the face" -- mostly earning eye rolls from his two older daughters. His youngest son Luke, however, is more impressionable, at least at first.

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* ''Series/{{Community}}'' introduces the one-off character Koogler, a middle-aged community college student who dresses and acts like he's the protagonist of an 1980s sex comedy. At one point he states that he knows what everyone says about him: "He's cool! He likes to get laid! He's [[SuspiciouslySpecificDenial not that old]]!"
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* ''Series/{{Community}}'' introduces a one-off character Koogler, a middle-aged community college student who dresses and acts like he's the protagonist of an 1980s sex comedy. At one point he states that he knows what everyone says about him: "He's cool! He likes to get laid! He's [[SuspiciouslySpecificDenial not that old]]!"

* Music/LCDSoundsystem's first big song, "Losing My Edge", is in the voice of an aging hipster desperately trying to keep up with the new scenes and is practically the theme song for this trope.

[[folder:Films -- Animated]]

* In the ''WesternAnimation/InsideOut'' short "Riley's First Date?", Riley's mother tries this during an attempt to casually ask about the eponymous date ("So, what's the dealio with Jordan? O-M-G, he is awesomesauce, fo'shizzy!"). Riley's Disgust is so, well, disgusted she [[ScrewThisImOuttaHere just walks away from the console]].

* ''WesternAnimation/SouthPark'': Zigzagged with Stan's dad Randy. He frequently jumps onto new trends just to look cool, often so he can rub his attitude in everybody else's face. For example, during Season 19, he joins the [[PoliticalCorrectnessGoneMad PC fraternity]] so he can act like a {{fratbro}}, get drunk, and then act morally superior to everybody else in the neighborhood, despite not actually understanding much about social justice. However, in some episodes, he does successfully manage to become popular in the eyes of the public, such as his stint as the pop idol Music/{{Lorde}}. There are also a few episodes where Randy stubbornly ''rejects'' trends, such as his insistence that the family run a Blockbuster store despite everybody else turning to the Internet, and his development of a weed farm to counteract the vaping trend. His family tends to find his behavior embarrassing no matter what.

* ''WesternAnimation/SpongebobSquarepants'': The main plot of Season 3’s * ''Mid-Life Crustacean'' is Mr. Krabs going on a night on the town with Spongebob and Patrick to prove that he’s still cool.

* ''WesternAnimation/SpongebobSquarepants'': The main plot of Season 3’s ''Mid-Life Crustacean'' is Mr. Krabs going on a night on the town with Spongebob and Patrick to prove that he’s still cool.

* ''WesternAnimation/SpongebobSquarepants'': The main plot of Mid-Life Crustacean is Mr. Krabs going on a night on the town with Spongebob and Patrick to prove that he’s still cool.

* ''WesternAnimation/SpongebobSquarepants'': The main plot of Mid-Life Crustacean is Mr. Krabs going on a night on the town with SpongeBob and Patrick to prove that he’s still cool.

* In ''ComicBook/XCellent'', Axel Cluney and Guy Smith are both washed-up former superheroes from the aughts who are trying to rebrand themselves as modern heroes in the 2020s. Axel tries to do it by embracing [[StrawCharacter various flavors of the alt-right]], like [[StrawMisogynist men's-rights advocates]] and Website/YouTube [[StrawCritic critics]]. Guy, on the other hand, goes in the opposite direction, courting a genderfluid vlogger named Girl Joe to endorse him and his teammates as the "woke" new team.

* In ''ComicBook/XCellent'', Axel Cluney and Guy Smith are both washed-up former superheroes from the aughts who are trying to rebrand themselves as modern heroes in the 2020s. Axel tries to do it by embracing various flavors of the alt-right, like men's-rights advocates and Website/YouTube critics. Guy, on the other hand, goes in the opposite direction, courting a genderfluid vlogger named Girl Joe to endorse him and his teammates as the "woke" new team.

* ''Series/ModernFamily'': Phil Dunphy tries to be the "cool" dad to his three kids, trying to stay hip to modern pop culture. He doesn't do very well -- he thinks WTF means "why the face" -- mostly earning eye rolls from his two older daughters. His youngest son Luke, however, is more impressionable, at least at first.

* In ''ComicBook/XCellent'', Axel Cluney and Guy Smith are both washed-up former superheroes from the aughts who are trying to rebrand themselves as modern heroes in the 2020's. Axel tries to do it by embracing various flavors of the alt-right, like men's-rights advocates and Website/YouTube critics. Guy, on the other hand, goes in the opposite direction, courting a genderfluid vlogger named Girl Joe to endorse him and his teammates as the "woke" new team.

'''Frasier:''' Please don't try to be hip. You remind me of Bob Hope when he dresses up as the Fonz.
* On ''Series/GregTheBunny'', Gil asks Jimmy how they can update "Sweetknuckle Junction" for a more modern audience. The result includes changing Count Blah into a rapper named Count A'ight (which he repeated mispronounces as ah-ig-it), sexing up Dottie, and painting Junction Jack silver, suspending him from the rafters, and renaming him Cybo-Jack. ("It's finally happened. They made me into a puppet.") They also add a strobe light effect which ends up giving the kids in the focus group seizures, resulting in them abandoning the retool.

* ''WesternAnimation/TheSimpsons'': The episode "Homerpalooza" revolves around this trope. After Homer embarrasses Bart and Lisa with his old-time rock and roll tastes (and they make it clear to him) he tries to become cool again in their eyes by taking them to the Lollapalooza music festival and accidentally becoming a freak show act. He does a prettty good job at it until he discovers that the stunt he's doing for the act ([[{{Kevlard}} catch cannonballs with his stomach]]) is destroying his innards and he quits, whereupon he is deemed "embarrassingly square" by the kids again.

* Music/LCDSoundsystem has their first big song "Losing My Edge", which is in the voice of an aging hipster desperately trying to keep up with the new scenes.

The [[TitleDrop Aging Would-Be Hipster]] is an older adult who tries too hard to be up-to-date by awkwardly adding the latest slang terms to his or her vocabulary and diving into the hottest trends and fashions. Characters covered by this trope include people who were once part of the scene but fell out years before and are now trying to get back in (despite having little or no idea of what's going on) and long-term [[{{Hipster}} hipsters]] who feel the world is drifting away from them. In either case, the character's attempts to prove they're relevant and "with it" are often desperate and usually a source of comedy.

This trope is often paired with a [[HollywoodMidLifeCrisis Hollywood Mid-Life Crisis]] and can overlap with PrettyFlyForAWhiteGuy and result in the character either talking like a JiveTurkey or SpeakingLikeTotallyTeen. The AmazinglyEmbarrassingParents trope frequently comes into play if the character has children. A character who is a CoolOldGuy or CoolOldLady will manage to avoid falling within this trope.

Compare with [[MusicAgeDissonance Music/Age Dissonance]] and [[AgeInappropriateDress Age-Inappropriate Dress]]. Similar trope to TotallyRadical but differs in that it only covers [[InUniverse In-Universe]] examples.

-->'''Niles:''' Who was that babe-o-rama?
-->'''Frasier:''' Please don't try to be hip. You remind me of Bob Hope when he dresses up as the Fonz.

[[folder:OtherInternet]]
* A common internet response when this is perceived to happen is a screenshot of a scene from [[Series/ThirtyRock 30Rock]] showing Creator/SteveBuscemi badly dressed as a teenager with a skateboard at a high school saying "[[https://knowyourmeme.com/memes/how-do-you-do-fellow-kids How do you do, fellow kids?]]".