When I was watching Eternal Sunshine of a Spotless Mind again recently, I was a bit distracted by the cast, because it’s one of those where a bunch of actors you know, or have since come to know, are gathered in one place (Tom Wilkinson, Kate Winslet, Jim Carey, Mark Ruffalo, Kirsten Dunst, David Cross, Elijah Wood & Jane Adams). I really like those sort of films, so I thought I’d mention a few others.
One that stands out is Ocean’s Eleven, because not only does the 2001 version have such a cast (George Clooney, Matt Damon, Brad Pitt, Julia Roberts, Don Cheadle, Casy Affleck, Andy Garcia, Bernie Mac and quite a few more), so did the original 1960 one, which was basically the infamous Rat Pack (Peter Lawford, Frank Sinatra, Dean Martin, Sammy Davis, Jr. and Joey Bishop).
Other great instances are St. Elmo’s Fire (Emilio Estevez, Andrew McCarthy, Judd Nelson, Rob Lowe, Ally Sheedy, Demi Moore, Andy MacDowell and Mare Winningham) which had an entire generation of actors in it, 10 Things I Hate About You which, while on a smaller scale, had faces that have popped up in TV and movies since (Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Gabriel Union, Susan May Pratt, Larissa Oleynik and David Krumholtz) and School Ties (Bredan Fraser, Matt Damon, Ben Affleck, Chris O’Donnell, Amy Locane, Cole Hauser and a bunch more). Then there’s Enemy of the State which has a surprising mix (Seth Green, Scott Caan, Jason Lee, Jack Black, Barry Pepper, Loren Dean, Ian Hart, Regina King, Will Smith, John Voight and Gene Hackman).
I’m sure there are even more examples (Grand Budapest Hotel!), but these are the ones that have stuck in my mind.