The world was stunned earlier this week when news broke of Matthew Perry’s passing. For portraying sarcastic, neurotic Chandler Bing for ten seasons – a whole ass decade, an entire era – on the hit sitcom Friends, Perry became a household name. His fame never wavered despite the ups and downs of his career.

While the darkest parts of Perry’s life were defined by his struggles with substance abuse – to the point that he claims no recollection of his time during the show’s third and sixth seasons thanks to painkillers – he was also known for his kindness and the support for others in the industry, as well as helping others get on the road to recovery from substance abuse.

All that being said, while there were many moments in his uneven career where he was bizarrely miscast or his talents wasted, Perry never phoned it in. From quirky Hollywood comedies to one of his favorite video games, Matthew Perry brought his best, even when he was at his worst. Here are eight of his most overlooked roles.

8. Numb (2007), as Hudson Milbank

In this comedy about a Hollywood screenwriter who struggles with depersonalization disorder, Perry shines. Director Harris Goldberg based the script on his own experiences with depersonalization. The result is a pretty hilarious but sometimes depressing film that seems almost tailor made for Matthew Perry, who can deliver every darkly sardonic light with the right comedic touch.

7. The Good Wife (2012–2013) / The Good Fight (2017), as Mike Kresteva

Probably the least likable character that Perry has ever added to his resume is the one he played on Michelle and Robert King’s legal procedural franchise. Perry plays a lawyer who despite his friendly demeanor, is a cutthroat operator who parlays his ruthlessness into a political career, constantly twisting the truth to befuddle and infuriate Alicia Florrick (Michelle Monaghan).

6. A Night In The Life of Jimmy Reardon (1988), as Fred Roberts

One of Perry’s earliest roles was as a rich kid from the suburbs in this coming-of-age drama headlined by River Phoenix. Perry played best friend to the titular character. As Jimmy Reardon, Phoenix plays a moody, literate middle-class kid who refuses the path to success that his business-minded parents have laid out for him. Filmed when he was 17, one can already see Perry’s deft comic timing.

5. Fallout New Vegas (2010), as Benny

On an appearance on Ellen, Perry described his addiction to Fallout 3 on the Xbox 360. An addiction, so bad it required him to go to a doctor to treat the damage his controller was doing to his hands. That appearance earned him the attention of Fallout publisher Bethesda which led to his casting in the follow-up game, 2010’s Fallout: New Vegas.

In it, he played a buffalo plaid-suited gangster who is one of many antagonists fighting to control the Mojave Wasteland. Benny uses various schemes to rig the odds in his favor. During the production and promotion of the game, game director Joshua Sawyer (Pentiment, Pillars of Eternity 2) said, “He’s really, really enthusiastic and a genuine fan.”

“Fallout is just bigger and smarter than any game that I’ve played,” Perry added. Fallout: New Vegas has spawned many memes, some of which include Perry’s lines like “The truth is… the game was rigged from the start,” and “You made your last delivery, kid.”

 4. Almost Heroes (1998), as Leslie Edwards

This critically drubbed period comedy pairs Perry with comedy legend Chris Farley, in which they play aspiring expeditioners trying to beat the renowned Lewis & Clark in crossing the United States to the Pacific Ocean. The movie is filled with slapstick, zaniness, and all the low-brow humor you’d expect from a late 90s comedy co-starring Chris Farley.

The film was a total commercial flop and while many involved would rather forget it, it feels wrong to not include this film on any list highlighting Perry’s career, especially as Perry found himself marketing the film on his own. Farley died of a drug overdose shortly before the film’s release.

The film is condemned to endless repeats on the slow hours of cable movie channels (and it wouldn’t surprise me if it were on Tubi), but remains bizarrely watchable. Despite being miscast as a foppish aristocrat and total dilettante, Perry serves as a fairly decent foil to Farley’s famously manic energy.

3. The Whole Nine Yards (2000), as Nicholas “Oz” Oseranski

Perry is known for injecting a nebbish quality into his characters. But he’s never nebbished as hard as he ever nebbished in these two comedies, in which he shares screen time Hollywood movie legends like Bruce Willis and Michael Clarke Duncan.

Matthew Perry plays a put-upon dentist whose life is thrown into chaos when a former hitman moves into his suburban neighborhood. Hijinks, as they say, ensue. While not every review was glowing for this film, it was successful enough, thanks to a cast that pulls off the film’s strange easygoing craziness. The box office was good enough to lead to a not-very-good sequel.

2. Fools Rush In (1997), as Alex Whitman

Probably one of the most sentimental films Perry has ever made. Perry plays a construction project manager who spends a one-night stand with Isabel Fuentes, a free-spirited photographer played by Salma Hayek. Their night results in an unexpected pregnancy, in which Alex and Isabel rush into a relationship with one another.

It’s an immensely watchable film buoyed largely by the energy that Perry and Hayek share together as their characters improvise the trials and tribulations of their relationship, while developing and deepening their feelings for one another. In his memoir, Perry said he considered Fools Rush In to be one of his best films.

1. Studio 60 on the Sunset Strip (2006–2007), as Matt Albie

One of many projects that feature insufferable white men developed by Aaron Sorkin, the celebrated screenwriter and co-creator of The West Wing. Despite a massive bidding war between NBC and Warner Bros, only a single full season of episodes of this show was produced, and only half the episodes aired before NBC pulled the plug.

Studio 60 is about a late-night variety show that airs live every Friday night. Perry plays a successful screenwriter while Bradley Whitford (Get Out, The Handmaid’s Tale) plays his creative partner Danny Tripp, both of whom are under tremendous pressure to rehabilitate the quality of the show. Like many Sorkin works it’s treacly, self-important, and filled with familiar tropes.

Despite all that, it’s a low-key favorite of this writer, who can’t get enough of Sorkin’s whip-smart dialogue and his utterly staged moral/intellectual debates. Perry is pitch-perfect for this, as a master at delivering any line you can throw at him. As Albie, Perry is asked to play a character who thinks before he shoots his mouth and faces the pressure of a network show with all the dark humor he can muster.

Did we miss your favorite Matthew Perry title? Tell us about them in the comments!