18. 'Don's Plum' (2001)
This no-budget, black-and-white indie (filmed from 1995 to 1996) was notable mainly for co-stars DiCaprio and Tobey Maguire attempting to stop it from being released in the wake of their newfound stardom. They shouldn't have been so worried: A talky, vignette-based story about a group of teens meeting in a diner called Don's Plum, R.D. Robb's film features numerous strong performances and a loose, improvisatory feel. But the film is also often undercut by random, irritating bits of arty, faux-poetic stylization, which mark it as a mid-Nineties curio — and because of its reputation and overall unavailability, a brief cause celebré when it screened at the Berlin Film Festival in 2001.