August 11, 2014 at 12:00 PM EDT

Robin Williams’ long filmography has more than its share of high-profile roles—but IMDb lists 102 total acting credits stretching all the way back to 1977. (That first one? A pair of parts in something called Can I Do It ‘Till I Need Glasses?, which the site describes as “a comedy are comprised [sic] of short sexually suggestive skits.”) Williams’ triumphs (Good Will Hunting) and failures (Popeye) are well-known, but it’s worth digging through some of his less-heralded work to find the occasional gem. 

1. Insomnia (2002)

Williams had been an animated Disney character, a silly cross-dressing nanny, Peter Pan, and an Oscar-winner before he accepted his first truly vile role. In Christopher Nolan’s psychological thriller, he plays a creepy killer who’s itching to take credit for his gruesome deeds, and his mano-a-mano with Al Pacino’s sleep-deprived L.A. cop becomes part of his sadistic game. Williams would follow up Insomnia with One Hour Photo, another unnerving performance that challenged audiences, but it was Insomnia that demonstrated how Williams could play the face of evil in the clear light of day.

2. What Dreams May Come (1998)

Critics weren’t kind to Vincent Ward’s highly stylized meditation on life, loss, and the afterlife. (“Heaven looks like nothing so much as a baroque series of progressive-rock album covers, and Robin Williams, sliding around in all that color, grows moist in the extreme,” wrote EW’s Owen Gleiberman.) What Dreams May Come wasn’t an easy sell: An entire family is wiped out, starting with the death of Williams and Annabella Sciorra’s children, then Williams, then capped off by Sciorra’s suicide. The film is more hopeful than that summary suggests—though the circumstances around Williams’ death make it more difficult to watch now—and Williams shows a dramatic depth that he was seldom able to explore. Gleiberman aptly described it as “achingly sincere.”

3. The Best of Times (1986)

Williams was still winnowing down his gonzo on-screen persona when he took the role of Jack Dundee, a sad-sack banker haunted by the sure-thing touchdown pass he dropped that would’ve won his high-school team the big game. 13 years later, with his marriage in shambles, he goes to insane lengths to get the star quarterback (Kurt Russell), his other out-of-shape teammates, and the rival school back on the field for a rematch he believes will reverse his town’s fortunes. It’s hardly a great Williams performance, nor would it make the short list of really good football movies, but there’s something very sweet and innocent about it—especially Williams’ hopeless dreamer.

4. Dead Again (1991)

Fresh off winning performances in Dead Poets Society and Awakenings, Williams popped up practically unannounced in Kenneth Branagh’s romantic thriller, playing against type as a squirrelly disgraced shrink who preaches cosmic forces and past lives to Branagh’s skeptical private eye. (He insisted his cameo go uncredited. “When we sent the script to him, he loved the part,” Branagh said at the time, “but he was determined to be unbilled so the audience would not perceive this as a Robin Williams film.”) Williams gives the character real verve, while sprinkling in a few subtle tics and a quick temper that made you want to follow him around at his grocery store for more than just two scenes.

5. Club Paradise (1986)

Williams said he did this film—about a Chicago fireman who moves to the Caribbean to open a hotel—more or less for a paycheck, but it was sneakily great: It was directed by Harold Ramis (coming off two stone-cold classics, Caddyshack and National Lampoon’s Vacation) and co-starred Rick Moranis, Eugene Levy, reggae legend Jimmy Cliff, early supermodel Twiggy, and Peter O’Toole (who was also cashing a check). Beyond that, the script’s four credited writers include not just Ramis and Brian Doyle-Murray (also of Caddyshack and appeared in small role) but also Harry Shearer. As Jack, Williams brought a funny weariness to the role of a resort owner in over his head, and found the jokes without the manic riffing that would become his signature style. Nearly 30 years later, Club Paradise is a footnote for everyone involved, but charming regardless.

Compiled by Jeff Labrecque and Kyle Ryan

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