Friday (1995)

Director: F. Gary Gray

"It's Friday, you ain't got no job, and you ain't got shit to do." This endlessly quotable film depicted a hilarious look at life in urban Los Angeles. Ice Cube's Craig Jones really held it down for West Coast style too, rocking a black flannel shirt and Nike Air Force 1s. Chris Tucker's Smokey was no chump either, sporting a pocket tee (with a gold chain, natch), backwards cap, chinos, and Chuck Taylors—an ensemble that wouldn't look out of place today.