Aging Would-Be Hipster

"There's nothing sadder than an aging hipster."

— Attributed to Lenny Bruce

The 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 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 Hollywood Mid-Life Crisis and can overlap with Pretty Fly for a White Guy and result in the character either talking like a Jive Turkey or Speaking Like Totally Teen. The Amazingly Embarrassing Parents trope frequently comes into play if the character has children. A character who is a Cool Old Guy or Cool Old Lady will manage to avoid falling within this trope.

Compare with Music/Age Dissonance and Age-Inappropriate Dress. Similar trope to Totally Radical but differs in that it only covers In-Universe examples.

Examples:

Comic Books

• The League of Extraordinary Gentlemen: Played for Drama with Mina Murray. Despite not physically aging, thanks to the eternal youth gained for herself and Alan Quatermain from Ayesha's immortality pool in Africa, Mina has begun acting this way by the time Century: 1969 takes place, trying to adopt the mannerisms and culture of the Hippie generation. It's actually implied to be because she doesn't age naturally anymore - despite physically being in her 20's, Mina is well over 90 years old by this point, and feels like a Victorian throwback, frozen in time while the world moves on without her. It begins to damage her relationship with Alan and Orlando, who she resents for being perfectly happy with immortality.
• In X-Cellent, 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 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.

Films — Animation

• In Shrek the Third, Shrek uses slang to try to talk to Arthur, who just freaks out further and screams "Help, I'm being kidnapped by a monster that's trying to relate to me!"
• In the Inside Out 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 just walks away from the console.

Films — Live-Action

• This trope is the core of The Internship in which two middle-aged salesmen whose careers have been made obsolete by the digital age try to get a coveted internship at Google.

Live-Action TV

• 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 not that old!"
• On an episode of Frasier, Niles makes a failed attempt to appropriate what he thinks is current teen-speak.
  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.
• In one episode of Friends, Joey auditions for the role of a 19-year old in a TV show. His attempts at getting into character involve wearing a backwards cap and saying things like "Sup with the wack Playstation sup!"
  Joey: So am I 19 or what?
  Chandler: Yes. On a scale of 1 to 10, 10 being the dumbest a person can possibly look, you are definitely a 19.
• On Greg the Bunny, 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 repeatedly 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.
• Insecure has an example with the fictional '90s Show Within a Show Kev'yn. A clip is shown of the modern reboot which features a character dressed as Colin Kaepernick kneeling and saying "Hashtag Metoo!"
• Kids in the Hall has a recurring sketch called "He's hip, he's cool, he's 45", in which a 45-year-old man does things like offer a joint to his son or a job applicant that he's interviewing, or installs a strobe light in the dining room and puts it on when he is having dinner with his family.
• The Librarians 2014: A somewhat-less sad version in Jenkins. In "...and the Apple of Dischord", Jenkins says the feud between Eastern and Western dragons was not unlike the hip-hop East Coast/West Coast rivalry of recent decades. The others, surprised, ask Jenkins if he's familiar with hip-hop, to which he says he is "paid in full." Jenkins, as we would learn at the end of the season, is an immortal Sir Gallahad of Arthurian legend, and over a millennia old.
• Modern Family: 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. Also, Cam and Mitchell find as the years go by that being gay and fabulous is a young man's game.
• The Muppet Show featured Geri and the Atrics, a rock group consisting of six elderly women who went on the show to sing "Hound Dog" and "Do Wah Diddy Diddy". (These episodes originally aired in 1979 which was well before the people who were young when the songs were new became elderly themselves.)
• The Newsradio episode "Office Feud" features the very white and middle-aged Bill McNeal doing ads for "Rocket Fuel Malt Liquor" and trying to use AAVE slang, much to the horror of black co-worker Catherine. Incensed after he refuses to stop doing the ads, she decides to troll him by giving him deliberately bad advice on how to sound more "authentic".
• On Superstore, the titular store, Cloud 9, adopts an animated mascot, MC Cloud, who awkwardly uses hip-hop slang and refers to the store as his "bae". He also seems to be in an inexplicable Inter Species Romance with a human woman.

Music

• The music video for the single "Dancin' In the Ruins" from the Blue Öyster Cult album Club Ninja has an uncomfortable visual air of this. While a tribe of late-teen skateboarders and dancers are performing to the music provided by the band, it becomes obvious that most of the band members are well into their forties and while they are playing some good hard rock, they are in the background, and not really interacting with the kids. It's almost as if the video director had thought "how do we make this relevant to the kids of today who will be watching this video on MTV?" and had the inspiration of "Skateboards" Kids dancing! It cannot fail!"
• LCD Soundsystem'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. When he isn't trying to boast about his past with (mostly fake) stories about influencing the underground music scene, he's chastising "the new kids" that got the window of fame that he himself never got, while also indirectly mocking himself for feeling so envious to begin with.
  I used to work in the record store, I had everything before anyone.
  I was there in the Paradise Garage DJ booth with Larry Levan.
  I was there in Jamaica during the great sound clashes.
  I woke up naked on the beach in Ibiza in 1988.
  But I'm losing my edge
  To better-looking people
  With better ideas and more talent.
  ...and actually, they're really, really nice.

Other

• A common internet response when this is perceived to happen is a screenshot of a scene from 30 Rock showing Steve Buscemi badly dressed as a teenager with a skateboard at a high school saying "How do you do, fellow kids?".

Western Animation

• Daria featured magazine editor Val who ran a magazine aimed at teens - and never stopped trying to act and dress like one despite being clearly over thirty.
• Gravity Falls: Grunkle Stan hates teenagers and makes no effort to hide this fact, but he invokes this trope twice in the hopes of attracting younger customers to the Mystery Shack. In "Double Dipper", he arranges a party at the Shack and shows up dressed out in laughably outdated Disco Dan clothes, but thankfully, having the 22-year old Soos DJ means the party ends up a success despite Stan's efforts. In "The Love God", he tries to cash in on the annual music festival, and because some of the attendants arrive riding hot air balloons, decides that teens therefore must all love hot-air balloons! The resulting patchwork mess ends up turning into a G-rated version of the Hindenburg disaster.
• The Simpsons: 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 pretty good job at it until he discovers that the stunt he's doing for the act (catch cannonballs with his stomach) is destroying his innards and he quits, whereupon he is deemed "embarrassingly square" by the kids again.
• South Park: 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 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 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.
• Family Guy: Brian occasionally comes across this way as part of his Know-Nothing Know-It-All personality. He claims to be "hip" to the latest teen and young adult trends, either to date younger women or generally act superior to his peers. In one case, he became a substitute teacher to a highly stereotypical group of underprivileged kids and tried using slang to talk about Romeo and Juliet as a feud between East and West Coast rappers. The unimpressed students immediately called him out on his racism.
• Spongebob Squarepants: 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.

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