Jason Segel’s career has come of age through the decades, even as he sometimes reverts to characters not quite acting their age — it’s kind of his thing.

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Starting with bit roles as an 18-year-old, including a still-memorable scene in Can’t Hardly Wait, he went on to gain notoriety for his performance in the Judd Apatow classic Freaks and Geeks, which launched many a career and has been revisited often. Segel had several roles on film and television that kept putting him on the verge of stardom, but it wasn’t until How I Met Your Mother that he really was able to gain a foothold in Hollywood, which has led to him writing and producing several hits of his own.

A talented musician and basketball player in his youth, Segel has melded those personas into several of his roles in which he gets to show his athleticism and musical chops, including the drums in Freaks and Geeks, piano in How I met Your Mother and Forgetting Sarah Marshall, and the guitar in I Love You, Man.

Though Segel has courageously taken plenty of risks throughout his career — including a bit of scene-stealing graphic nudity in the first film he wrote, Forgetting Sarah Marshall — there has been a lack of consistency in his roles at times. That all seems to be coming to a head with this year’s release of Shrinking, which has shown promise and could evolve into a well-rounded show that takes on the ultra-tangible modern relationship of therapy, and people struggling to come to grips with the world around them that seems devoid of, well, so many things.

From TV to movies, Segel has given fans a lot to root for over the years, and here are his top 10 performances so far.

10. Windfall (2022)

The fifth and most recent movie written by Segel is his best since The Muppets. Definitely better than Sex Tape or The Five-Year Engagement (which are both average at best), Windfall is saved by its supporting cast around Segel — namely, the impeccable Jesse Plemons and the underrated Lily Collins. The movie is about a wealthy couple, played by Plemons and Collins, who happen upon an intruder in their home, played by Segel. Interestingly enough, nobody has a name in the movie, with the characters called CEO, Wife, and Nobody, respectively. It’s a thriller that’s a little light on thrills, with plenty of exposé and revelatory dialogue between the three players.

9. Our Friend (2019)

Another film that really becomes worthwhile thanks to the performances involved. The movie is biographical and based on a magazine article of all things, following the story of a couple who are facing insurmountable odds. The couple — Matt and Nicole — played by Casey Affleck and Dakota Johnson, set out to tell their daughters about Nicole’s terminal cancer. Their best friend, Dane, played by Segel, is intertwined with their lives and through flashbacks that come up to the current day and beyond, we see the love and affection the trio has for each other.

8. Jeff, Who Lives at Home (2011)

An indy film directed by the Duplass brothers, Jeff, Who Lives at Home gave Segel a chance to show off his more sensitive and sorrowful side coming on the heels of his success in the comedy genre. Segel plays Jeff, who is unemployed and in his 30s still living at home with his mom – played masterfully by Susan Sarandon. Jeff finds reason in randomness — thanks to the movie Signs — and he begins looking for signs and following them, which leads him to some unfortunate situations. Judy Greer and Ed Helms bring a lot to their costarring roles as well, giving the movie a good balance of seriousness and lightheartedness. Overall, it’s a worthwhile watch, and if you’re familiar with the Duplass brothers’ work, then the interplay of characters will feel right at home.

7. Shrinking (2023-)

The show built a lot of buzz because of the people involved — rising star Brett Goldstein of Ted Lasso fame helped create the series along with Bill Lawrence and Segel, plus Harrison Ford was slated to costar in the show alongside Segel. While the reviews have been a bit scattershot so far — with some loving the performances and plot lines, and others feeling it falls into stale tropes too often — the show has proven riveting. Segel plays Jimmy Laird, a therapist who is going through his own trauma and grief following his wife’s death. Laird copes by telling his patients exactly what he thinks with total honesty, which is seen as an ethical breach in some ways by those around him.

6. Freaks and Geeks (1999-2000)

A cult classic that seems to only gain traction in popularity as the years go on, Freaks and Geeks made quite an impression in its short TV run. Segel’s character, Nick Andropolis, has a great sense of humor and is passionate about music, mimicking Segel’s real life, which is a big reason the role feels so believable. Nick displays common teen conflicted emotions of wanting to be his own person and break the cycle of what his parents want for him, while also trying to make them proud.

5. I Love You, Man (2009)

The interactions at the core of I Love You, Man made the movie a hit with audiences, which earned more than double its budget. The performance from Paul Rudd is really the star here, but his chemistry with Segel is pal-pable (sorry) and their running bits of dialogue and shared musical interests are extremely engaging. Segel’s character, Sydney, seems to be out for himself, but in the end he winds up being a softie who helps boost Peter Klaven’s (Rudd) career. The bits with Lou Ferrigno are unforgettable, and it’s a great cast all-around, featuring Rashida Jones, Andy Samberg, J.K. Simmons, Jane Curtin, Jon Favreau, and more.

4. The Muppets (2011)

On the heels of writing and starring in his first movie, Segel wanted to tap into his childhood love of the Muppets. Along with Nicholas Stoller, Segel pitched the movie to Walt Disney Studios and earned approval to develop a script, and the film went on to be wildly successful with both kids and adults. Starring a plethora of well-known Hollywood stars, including Amy Adams, Rashida Jones, Jack Black, Zach Galifianakis, and Donald Glover, Segel was able to portray the wonder of the original Muppets with a modern-day flavor. He plays Gary, a human who is the older brother to Walter, a Muppet. The two, along with Gary’s girlfriend Mary, go to Muppet Studios, where they overhear the plot for the movie: the Muppets could repurchase their old theater if they raise $10 million, however, an oil tycoon has other plans to actually purchase and destroy the theater so he can drill on the site for oil.

3. Forgetting Sarah Marshall (2008)

The first movie that Segel wrote was well-received and ended up performing better than expected. Forgetting Sarah Marshall was the launching point for his career and the freedom to continue writing roles and stories that he was interested in and control his own fate – as he was growing disinterested in the projects he was being offered and was hesitant to be boxed in. As Peter Bretter, his character goes through a breakup and heartbreak that leads to him fleeing to Hawai’i, where coincidentally, his ex is also vacationing. The heart of the story is the genuine chemistry between Segel and Mila Kunis, and Russell Brand does a phenomenal job as an annoying AF twit.

2. How I Met Your Mother (2005-2014)

Although Segel might have had stronger standalone performances, the breadth of acting he brings to the table as Marshall Eriksen throughout the nine-season run of How I Met Your Mother allowed most of the work he did during and since to come to fruition. From playing the goofy best friend, to suffering through depression and heartbreak with the death of his father on the show, to being a voice of reason as a lawyer, Segel gave one of the stronger TV performances of the past couple decades.

1. The End of the Tour (2015)

The movie that most sticks out from the rest for Segel, in which he received heaps of praise and accolades for his portrayal of the late author David Foster Wallace is The End of the Tour. Costarring Jesse Eisenberg, the movie handles the serious and grave subject matter of Wallace committing suicide through a revisitation of his life and work. Eisenberg plays writer and author David Lipsky, who wrote the book Although of Course You End Up Becoming Yourself – based on conversations between himself and Wallace recorded in the late 1990s.

Segel won the Independent Spirit Award for Best Male Lead and he, Eisenberg, and the film received several other independent award nominations as well. Segel’s portrayal of the author, who wrote Infinite Jest and The Pale King — among others — is worth watching whether you’re familiar with Wallace or not. And for any fan of Wallace’s work, the movie does him and the subject matter justice.