Andy Samberg has proven himself to be one of the most iconic and hilarious comedic actors of the 21st century, with a great number of iconic comedic performances already under his belt. From his early days doing musical sketch comedies like The Lonely Island and Saturday Night Live to his modern-day series roles in shows like Brooklyn Nine-Nine, Samberg has a distinct comedic voice that shines in nearly every one of his performances. There is no greater visualizer and showcase of Samberg’s greatest comedic attributes than his multitude of roles in film over the years.

Samberg has lent his comedic talents to a number of great comedic movies over the years, whether it be being one of many comedic actors in a studio comedy, or a major part of a film he produced himself. He also has a surprisingly high number of voice-acting roles in movies over the years, most recently shown off with his surprising appearance in Spider-Man: Across the Spider-Verse. Samberg continues to delight with his comedic chops in a wide variety of movies across his filmography and will continue to charm audiences with a number of upcoming releases.

10 ‘Chip n’ Dale: Rescue Rangers’ (2022)

Director: Akiva Schaffer

Chip n’ Dale: Rescue Rangers follows the titular dynamic chipmunk duo decades after their successful television series was canceled, with the two of them having drifted apart in their own Hollywood careers. However, when a former cast mate of theirs mysteriously disappears, the duo must repair their fractured friendship and take on their detective personas once again in order to solve this real-life case.

Samberg plays the role of Dale in the film, the more laid back and sporadic of the duo who, during his time after the show, underwent expensive CGI surgery in order to keep up with the times. While definitely a different style of character when compared to the original Dale, Samberg does a great job of bringing both his own comedic stylings and the signature character traits of Dale to the new version of the character. His great vocal chemistry with co-star John Mulaney is one of the highlights of the movie, as the dynamic between the duo is core to Chip and Dale as characters.

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9 ‘Celeste and Jesse Forever’ (2012)

Director: Lee Toland Krieger

Celeste and Jesse Forever follows the story of long-time romantic partners Celeste and Jesse (played by Rashida Jones and Samberg), who met in high school and got married at a young age. They seemingly appear to be the perfect couple to nearly everyone they meet, completing each other and seeming to be the textbook definition of true love. However, the duo has also been separated for nearly six months, despite still constantly being in each other’s lives and continuing to be each other’s best friends. Their situation soon has Celeste reevaluating their breakup in the first place, especially when Jesse seems to have met someone else.

Samberg plays the role of Jesse in the film, the best friend and seemingly perfect match for Celeste who has moved on with his life and to another relationship. Samberg and Jones already share a great deal of comedic screen time with each other, both playing recurring characters on Brooklyn Nine-Nine, and Celeste and Jesse Forever features even greater chemistry and back and forth between the two. The film is one of the more underrated romantic comedies of the 2010s, and features a number of both great comedic moments as well as genuinely heartfelt moments.

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8 ‘I Love You, Man’ (2009)

Director: John Hamburg

I Love You, Man follows the story of Peter Klaven (played by Paul Rudd), a successful real estate agent who was recently engaged to the woman of his dreams, Zooey, and begins planning their wedding. They soon come across a hiccup when they realize that Peter has no male friend close enough to be considered his best man, putting Peter on a quest to set out into the world and find a new best friend. He soon finds himself embarking on a number of increasingly strange and awkward “man-dates” in his quest to find the perfect best man.

Samberg plays the role of Robbie in the film, Peter’s gay younger brother who helps him and provides him with advice when it comes to meeting men for his quest to find a best man. While not the most important or integral part of the story, Samberg still provides a great deal of comedic moments and insight throughout the film, bouncing off of both Rudd and other supporting characters in the film. Even as just a smaller part of the film, his inclusion and role in the film further the film’s still relevant themes and message about male friendship and comradery.

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7 ‘Brigsby Bear’ (2017)

Director: Dave McCary

Brigsby Bear follows the story of James (played by Kyle Mooney), who has been a massive fan of Brigsby Bear Adventures, a children’s TV show, for the majority of his life. However, after it is revealed that the show was produced entirely for him and only him, the show has its abrupt end, changing the course of James’s life forever. James soon sets off on his own journey of finishing the story of Brigsby Bear himself, so that he can finally attain the closure that he never received.

Samberg plays the role of Eric in the film, one of James’s friends that he makes after discovering the truth about Brigsby Bear, and ends up helping him with his creation of the Brigsby Bear movie.

The film as a whole gracefully touches upon the importance of friendships and interpersonal relationships and how they make an impact on isolated and lonely people. Samberg plays one of many seemingly simple characters in the film that, in reality, have a major impact on James and the overall message and power of the film’s core themes.

Rent on Prime Video

6 ‘Tour de Pharmacy’ (2017)

Director: Jake Szymanski

Tour de Pharmacy is a sports mockumentary that follows the fictional events surrounding the Tour de France in 1982, famous for nearly every contestant in the race using performance-enhancing drugs. The realistic yet highly absurd documentary retelling of the events cycles between the live coverage and interviews during the event, with comedic modern-day interviews reminiscing on the event featuring the likes of Mike Tyson, J.J. Abrams, and Lance Armstrong.

Samberg plays the role of Marty Hass in the film, the proclaimed greatest cyclist from Nigeria, but only attained said title because of being the son of an infamous blood diamond owner. He has a massive ego and cocky attitude towards his skill on the track, despite being one of many cyclists doping on the track, as well as every citizen of Nigeria hating his guts and how he toys with their country. As always, Samberg provides a great number of strange and hilarious comedic moments throughout the film, given a further layer of comedy with the interviews of the modern-day Marty Hass, played by Jeff Goldblum.

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5 ‘Hotel Transylvania’ (2012)

Director: Genndy Tartakovsky

Hotel Transylvania follows the story of a lavish and highly pristine hotel run specifically for monsters as their escape from running away or haunting humans, run by the legendary Count Dracula. However, during what may be the most important time in the hotel’s history, when they are celebrating Dracula’s daughter’s 118th birthday, an ordinary human stumbles upon the hotel. Being unable to simply get him to leave, it soon becomes of the utmost importance to have him blend in with the surrounding monsters, so as not to reveal himself and put the entire hotel in a state of panic.

Samberg voices the character of Johnny in the film, the laid-back ordinary hiker who miraculously finds his way to Hotel Transylvania after wandering off the beaten path. As the Hotel Transylvania series continued to grow in popularity with numerous sequels and spinoffs, Samberg would continuously reprise his role as one of the core main characters of the series. Samberg’s easygoing attitude and mannerisms work perfectly for the character of Johnny, and his comedic timing and rendition of the character are some of the many reasons the series has continued to find success over the years.

Rent on Prime Video

4 ‘7 Days in Hell’ (2015)

Director: Jake Szymanski

7 Days in Hell is a sports mockumentary that follows the match between fictional rivals Aaron Williams and Charles Poole, as they battle in an increasingly strange tennis match that lasted 7 days. The match has a wide range of twists and turns, each more strange than the last, from streakers running the field to multiple instances of attempted sabotage off the field. The film features a number of interviews with modern-day celebrities, including Serena Williams, John McEnroe, and David Copperfield, who look back upon the events of the match as if it were a real event.

Samberg plays the role of Aaron Williams in the film, titled “Bad Boy of Tennis” and is the fictional third adopted member of the Williams family. He brings his signature wild and unpredictable comedic style to a character that is greatly defined by his unpredictability and brash nature. His comedic styling works perfectly alongside his opponent, played by Kit Harington, whose more shy and socially awkward comedy style is a hilarious parallel to the in-your-face comedy style of Samberg.

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3 ‘Hot Rod’ (2007)

Director: Akiva Schaffer

Hot Rod follows the story of Rod Kimble, an amateur stuntman who considers his work a way of life, despite the lack of respect he receives from the community and his stepfather, Frank. However, when Frank’s heart troubles catch up to him and his time on Earth is cut short, Rod does everything he can to use his stuntwork to raise money so that he can pay for Frank’s procedure. Both so he can finally prove that he is worth to Frank, and being able to kick his butt before it’s too late, Rod and his friends plan on taking their stunts to the next level.

Samberg plays the lead role of Rod in the film, with a notable comedic performance that uses his nativity and unawareness of his surroundings to result in a great deal of awkward and slapstick comedy. The style of comedy and humor in Hot Rod is somehow simultaneously extremely of its era of the late 2000s while also having aged incredibly well with the style of humor surrounding the internet as a whole. The film exudes a level of stupid yet lovable comedy that makes it one of the best comfort movies of all time, and one whose biggest fans consider it one of the best of all time.

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2 ‘Palm Springs’ (2020)

Director: Max Barbakow

Palm Springs follows the duo of Nyles and Sarah, one being a carefree spirit and the other being the maid of honor, attending what should be a normal Palm Springs wedding. However, things quickly get complicated when the duo find themselves trapped in a never-ending time loop, forced to relive the wedding day over and over without any chance of escaping. The duo soon become close friends as they do everything they can possibly think of at the wedding, yet as the truth comes to show, their friendship starts to show cracks as a result of its authenticity.

Samberg plays the role of Nyles in the film, the carefree goofball who finds himself at the center of this Groundhog Day-esque time loop. However, unlike Bill Murray in Groundhog Day, Samberg’s performance is much more comedic and satirical in its similar state of despair and infinite self-loathing. The result truly does make Palm Springs the modern, millennial equivalent to a film like Groundhog Day, complete with all the intricacies and self-deprecating aspects of the more modern generations.

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1 ‘Popstar: Never Stop Never Stopping’ (2016)

Directors: Akiva Schaffer, Jorma Taccone

Popstar: Never Stop Never Stopping is a music mockumentary that follows worldwide pop sensation Conner4Real just as he’s hitting a major downward spiral in his career. As he attempts to recapture the magic that came about during the early years of his career, every attempt to save face and make successful new songs on his new album ends up being an even bigger disaster. With nowhere else to turn, Conner ends up having to face the facts and return to the origins of his career, his old rap group, The Style Boyz.

Samberg plays the lead character of Conner4Real, a character who embodies all the stereotypes and negative conceptions surrounding pop stars and pop star culture in the 2010s. On top of leaning into Samberg’s more satirical strengths as a comedy actor, the film as a whole feels like a complete embodiment and love letter to Samberg’s career as a whole. The film was directed by and stars his fellow Lonely Island members Jorma Taccone and Akiva Schaffer, and the film feels like a feature-length version of one of their hilarious song parodies. While he has surely had more successful and notable films and shows during his comedy career, there is no other movie that defines Andy Samberg quite like Popstar: Never Stop Never Stopping.

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