After landing his breakout role as Nick Adopolis in Freaks and Geeks, Jason Segel has propelled quite the acting career. Although he's been involved with some major flops like Sex Tape (2014), Jason Segel will always prevail as one of the funniest, most lighthearted comedy actors for his time.
Though Freaks and Geeks may have given him his first breakout role, the actor has come a long way since playing that rebellious teenager. From playing Marshall Eriksen in How I Met Your Mother to Playing David Foster Wallace, Segel's career has taken him to some unexpected places.
Watermelon Guy: Can't HardlyWait (1998)
Short but sweet, Jason Segel's role as 'Watermelon Guy' in the late '90s coming-of-age film Can't Hardly Wait was his very first! This 'Watermelon Guy' is found sitting next to his stoner buddy at the main high school party, centered throughout the movie... eating a watermelon of course! After Amanda Beckett (Jennifer Love Hewitt) receives a love letter from a classmate she can't remember, Preston (Ethan Embry), she asks Watermelon Guy and his friend if they know him.
A hilarious scene proceeds of these two goofballs explaining every other white male with brown hair, and ends with Watermelon Guy's friend giving credit to Velma from Scooby-Doo, saying "you know who else I like, but never got much play?"
Nick Andopolis: Freaks And Geeks (1999-2000)
Freaks and Geeks will forever encapsulate the quintessential cult-classic TV show that was canceled after an almost-perfect first season. Jason Segel's character, Nick Adopolis, was a staple of the main cast, playing main protagonist Lindsay Weir's (Linda Cardellini) love interest. Linda Cardellini and Jason Segel dated in real life for five years.
Though it wasn't his first role, Freaks and Geeks was Jason Segel's first big break, and where he met Judd Apatow and Seth Rogen (his debut performance), who helped launch his career. The series receives an 8.8 on IMDb, regardless of only being eighteen episodes long. Watch his audition tape here.
Eric: Undeclared (2001-2003)
This Judd Apatow gem received a lot less attention than its sister-show Freaks and Geeks and deserves more recognition. Starring Jay Baruchel as insecure Steven Karp, who starts his freshman year of college the same day he loses his virginity to fellow freshman cutie, Lizzie (Carla Gallo). The only problem? Lizzie's long-distance older boyfriend Eric (Jason Segel) is still trying to make things work with her, and he's...insane.
Jason Segel does an excellent job portraying the over-the-top wackiness Eric conveys throughout his time on Undeclared. The scene where he scream-raps Mystikal's 2000 hit "Danger (Been So Long)" never gets old. Ben Stiller ends up playing Eric's ex-stepfather and makes this show a worthwhile watch just for the great cameos, which also include Adam Sandler, Amy Poleher, and Mike White.
Leon: 11:14 (2003)
Though his role in 11:14 is also small, the movie is impactful. Focused around five different character's perspective of the events leading up to 11:14 PM, the film stars some heavy hitters, including Hilary Swank, Patrick Swayze, Colin Hanks, Ben Foster, and Rachael Leigh Cook.
Jason Segel plays a paramedic named Leon alongside his co-worker Kevin, and the two respond to the accidents that a few teenagers (and others connected) caused in a small town. The movie received a 7.2 rating on IMDb, but if Jason Segel is your main draw, skip this choice.
Marshal Eriksen: How I Met Your Mother(2005-2014)
Jason Segel seems perfectly fit for the role of Marshall Eriksen, but maybe Marshall Eriksen is so lovable because Jason Segel gets to portray him! The harmless, hopeless romantic in Marshall won over the hearts of fans, his relationship with wife Lily Aldrin (Alyson Hannigan) is one of the greatest love stories in 21st-century television.
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How I Met Your Mother ran for an impressive 9 seasons, and much like its Friends counterpart, each member of the gang is featured in every single episode! Alyson Hannigan gave a heartwarming interview on The Talk about no longer working alongside her work-husband Jason Segel, tearing up in the process!
Peter Bretter: Forgetting Sarah Marshall (2008)
Jason Segel writes and stars as the main character Peter Bretter in this exceptional 2008 comedy, Forgetting Sarah Marshall. After a hurtful breakup with long-term girlfriend Sarah (Kristen Bell), Peter takes the advice of his brother Brian (Bill Hader), and vacations to a resort in Hawaii. Much to Peter's dismay, Sarah seems to be staying at the same resort, with her new rockstar boyfriend Aldous Snow (Russell Brand).
With the help of front-desk staff Rachel (Mila Kunis) and Matthew the Waiter (Jonah Hill), Peter finds himself enjoying life without Sarah and learns to cope with his newfound independence. Forgetting Sarah Marshall acts as the prequel to Get Him to the Greek (2010), which also stars Jonah Hill and Russell Brand as Aldous Snow, the very same character.
Sydney Fife: I Love You, Man (2009)
This whimsical comedy stars Paul Rudd as newly betrothed Peter Klaven who finds himself friendless and in need of a Best Man for his wedding. After a string of miserable bro-dates, Peter meets the elusive real estate agent Sydney Fife, and the two hit it off immediately.
Enraptured by Sydney's carefree lifestyle, Peter's relationship with his fiancee Zooey (Rashida Jones) is endangered, and Peter has to find a balance between romance and bromance. Also starring Jon Favreau and Jamie Pressly as their diabolical couples-friends, I Love You, Man will guarantee to make you chuckle.
Jeff: Jeff, Who Lives At Home (2011)
Jason Segel stars as the unmotivated slacker Jeff, who, while out on an errand for his widowed mother who he lives at home with, tries to find answers from the universe after taking cues from his favorite movie, Signs (2002). Jeff runs into his hotshot salesmen brother Pat (Ed Helms) and discovers his marriage might be in jeopardy.
A thought-provoking film from the critically-acclaimed Duplass brothers, Jeff, Who Lives At Home received a 6.5 on IMDb. Also stars Susan Sarandon, Judy Greer, and Steve Zissis.
Tom Solomon: The Five Year Engagement (2012)
Segel co-wrote this film with its director, Nicolas Stoller (Friends From College) and also stars as the main protagonist Tom Solomon, who proposes to his psychologist girlfriend, Violet (Emily Blunt). After she receives a job offer in Ann Arbor, Michigan, the couple uproots their San Franciscan lives, running into detours that postpone their nuptials.
Growing further apart, the couple examines their true intentions in The Five Year Engagement. Chris Pratt and Alison Brie star in the film, which receives a 6.5 on IMDb.
David Foster Wallace: The End Of The Tour (2015)
Based on the true story of David Lipsky (Jesse Eisenberg), a Rolling Stone reporter who interviews the famous author David Foster Wallace (Jason Segel) over the span of five days in 1996. Both Segel and Jesse Eisenberg received high praise for their performances in The End of the Tour, which only gets a 7.5 on IMDb but scores 92% on Rotten Tomatoes.
The End of the Tour is a more serious role for Jason Segel, which sets up a nice change in tone, rather than his standard trope: the needy boyfriend in a rom-com. Segel did plentiful research on David Foster Wallace before portraying him in the film.