- "Stop giving me that pop-up ad for Classmates.com! There's a reason you don't talk to people for 25 years, because you don't particularly like them! Besides, I already know what the captain of the football team is doing these days: Mowing my lawn."— Bill Maher, New Rules
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- Wayne and Garth from Wayne's World are High School Rejects, albeit unusually sympathetic ones.
- Jay and Silent Bob from The View Askewniverse.
- Played with fairly frequently in Kevin Smith's work, come to think of it.
- Also Dante and Randal, T.S. and Brodie, Zack and Miri,...Holden and Banky are a subversion, though.
- Biff in Back to the Future, after Marty's influence. And again in the second part.
- Uncle Rico, in Napoleon Dynamite who mentally relives his high school football playing glory days, while cooking up various schemes to make money, all of which are degrading and ineffective.
- Tommy and Darian, in Beautiful Girls. Tommy was a hockey star destined to be a snow plower. Darian was an Alpha Bitch destined for an unhappy marriage. Though popular in high school, they are miserable adults, and the affair between the two of them ruins their lives further.
- The Party's Over by Caroline Cooney documents an Alpha Bitch's transition to this as her refusal to plan for the future catches up with her.
Live Action Television
- Cold Case adores this trope.
- Eddie Winslow's friends Willie and Weasel on Family Matters. Waldo Faldo was this too when he was introduced in the series but evolved into Eddie's best friend and was given a job and a girlfriend.
- Invoked by the AV club faculty advisor in Freaks and Geeks.
- Tim from One Tree Hill was an annoying basketball player. Four years after graduating, it is revealed in season 5 that he is now a pizza delivery man.
- One of these is one the first victims (possibly the very first) to be killed by a meteor freak in Smallville.
- The Beavis And Butthead rip-offs on Step by Step.
- Weevil from Veronica Mars is a High School Reject who quickly became a major supporting character. When the show moved on from high school, he did indeed fail to get his diploma (due to being arrested at graduation) and instead has had several casual jobs, the first of which was in a gas station.
- Frank Zappa's song "Wind Up Working In A Gas Station" could be a trope namer.
- Bruce Springsteen's "Glory Days" gives several examples.
- The Statler Brothers' "Class of '57" mentioned several of these in their list of graduates and what became of them.
- Not high school, but this trope was invoked in Frazz, after Caulfield has a run-in with the school bully:
Frazz: Cheer up, by the time you're thirty, he'll be working for you.Caulfield: Maybe I don't want to manage a Boo-Boo Burger franchise when I grow up!
- Parodied in Family Guy in which Brian, as a teacher, calls out his disobedient students and tells them that they will become this trope if they continue. Cue them being interested in the idea of living low-end jobs, stand on their desks and say "Oh captain, my captain!"