Films and TV shows with prescient casting

[Hot Pepsi]

Freaks & Geeks and, to a lesser extent, Undeclared launched the Apatowverse.

[Incandenza]

As elguapo4 notes, The Outsiders is a pantheon in prescient casting, but Wet Hot American Summer (2001) runs it close. It's a (really quite poor) parody of summer camp/teen coming of age/sex films, but the cast...
David Hyde Pierce would have been a billboard name due to Frasier, but it also starred Janeane Garofalo, Paul Rudd, Bradley Cooper, Chris Meloni (SVU), Elizabeth Banks, Amy Poehler, and a fair few others from various comedy troupes (mainly The State, but also SNL) who I'd probably recognise by face if not name.

Janeane Garofalo was already well-known for an indie comic at that time, being on the Ben Stiller Show in the early 90s (speaking of which, the Ben Stiller Show--Ben Stiller, Janeane Garofalo, Bob Odenkirk, and Andy Dick. Dick never became big, but the rest did), Larry Sanders Show, and smaller movie roles like Reality Bites. She was also on one season of SNL that was universally regarded as awful and lead to a lot of "is this the end of SNL?" pieces.

Paul Rudd was in Clueless, don't forget that.

[sw2borshch]

I am stretching to include this, but have been watching the Lavender Hill Mob this evening and was a little taken aback by the brief appearance of Audrey Hepburn very early on.

[sw2borshch]

Possibly more NA-centric than I'd thought. All of them are big in '80s / '90s comedy films and TV shows. Paul Schaffer was tv host David Letterman's band leader for 30+ years. Levy and O'Hara are 'currently' starring in Schitt's Creek.

I know Gilda Radner from the name check in Night Night Theme by The Infesticons.

https://youtu.be/geyIAGNc2zM

[WOM]

Gilda's biggest fame was on Saturday Night Live for a few seasons. She was married to Gene Wilder and died young of cancer.

[Patrick Thistle]

Janeane Garofalo was already well-known for an indie comic at that time, being on the Ben Stiller Show in the early 90s (speaking of which, the Ben Stiller Show--Ben Stiller, Janeane Garofalo, Bob Odenkirk, and Andy Dick. Dick never became big, but the rest did), Larry Sanders Show, and smaller movie roles like Reality Bites. She was also on one season of SNL that was universally regarded as awful and lead to a lot of "is this the end of SNL?" pieces.

Paul Rudd was in Clueless, don't forget that.

Janeane Garafalo was (briefly) Jerry's fiancee in Seinfeld.

[Incandenza]

Yep!

[Hot Pepsi]

Paul Rudd was in Clueless, don't forget that.

That was/is a huge movie but Rudd is really the only member of the young cast that has gone on to a big career. Alicia Silverstone has done ok, but nothing she's done is nearly as well-liked as that. Stacy whatserface is a Fox Pundit, apparently. Brittany Murphy was on track for a good career, but died suddenly. Donald Faison did Scrubs, of course.

Another example of that is Dawson's Creek. I don't think many people would have guessed that any of the main cast would become "serious actors," but if they did, they probably wouldn't have guessed it would be Michelle Williams, who was originally just supposed to be the "blonde" that the protagonist is distracted by for a while before ending up with the girl next door. All four of the main cast are at least still acting and doing ok, but she has four Oscar nominations, two Golden Globes and an Emmy.

Mean Girls went 2/6, by my count. Rachel McAdams and Amanda Seyfried are both a pretty big deal and Lizzy Caplan has done very well, but Lindsay Lohan famously flamed out, whatsherface who plays Gretchen does Hallmark films now, the kid who played the dreamy crush guy is now a personal trainer in LA (I don't just know that trivia. It was mentioned on the Rewatchables about Mean Girls).

I don't know what became of the guy who played Damian, but IMDB said he's still acting in a bunch of stuff that I don't recognize.

The kid who played Kevin apparently quit the business after Mean Girls, but the actress who played the "Crying Girl" who "Doesn't Even Go Here!" is still in the business (https://www.imdb.com/name/nm1705724/?ref_=tt_ch)

Amy Poehler was also in that before she became a massive star, but she wasn't unknown. She was already on SNL, but not on Update yet, and she'd been in Wet Hot American Summer.

[Nocturnal Submission]

Possibly more NA-centric than I'd thought. All of them are big in '80s / '90s comedy films and TV shows. Paul Schaffer was tv host David Letterman's band leader for 30+ years. Levy and O'Hara are 'currently' starring in Schitt's Creek.

Even more famously (well, for me anyway), Shaffer was Artie Fufkin in Spinal Tap.

[Patrick Thistle]

Another example of that is Dawson's Creek. I don't think many people would have guessed that any of the main cast would become "serious actors," but if they did, they probably wouldn't have guessed it would be Michelle Williams, who was originally just supposed to be the "blonde" that the protagonist is distracted by for a while before ending up with the girl next door. All four of the main cast are at least still acting and doing ok, but she has four Oscar nominations, two Golden Globes and an Emmy.

She was in Venom, which was a much better comic book movie than I expected.