Top 10 Rewatchable Comedy Movies of the 2000s

The dawn of the 2000s heralded a vibrant cultural shift, characterized by audacious fashion trends, an explosion of innovative music, and a series of remarkable comedy films. This era, while home to a few forgettable titles, also witnessed the rise of influential creators like Judd Apatow, Tina Fey, and Ricky Gervais. These figures were instrumental in crafting some of the most notable R-rated comedies of the decade, defining a new standard for the genre that would leave a lasting legacy. Although certain jokes from this time may not resonate as effectively today, many films remain entertaining upon repeated viewings.

Featuring performances from emerging talents such as Jason Segel, Seth Rogen, and Michael Cera, the comedies of the 2000s showcased a blend of future stars and established names like Reese Witherspoon and Sandra Bullock. Their contributions produced some of the decade’s most memorable films, each celebrated for their commercial success, often grossing over $100 million despite modest budgets. In addition to blockbuster hits, the era also produced several underrated films that continue to garner appreciation from discerning audiences.

10 Not Another Teen Movie (2001)

Directed by Joel Gallen

The spoof genre thrived in Hollywood throughout the late 20th century, with films like Airplane! and Robin Hood: Men in Tights parodying various cinematic norms. This trend transitioned into the new millennium with Not Another Teen Movie, which humorously dissected the popular teen film genre. Starring Chyler Leigh and a pre-Marvel Chris Evans, the movie mainly parodied She’s All That, while referencing an array of beloved teen films.

Its clever mix of humor, including nods to Bring It On and Jawbreaker, reignited the spoof trend, leading to films like Vampires Suck and Scary Movie.Not Another Teen Movie stands out as a fun exploration of the genre, rich with nostalgic callbacks.

9 Pineapple Express (2008)

Directed by David Gordon Green

The chemistry between real-life friends often translates into captivating on-screen dynamics, a phenomenon clearly showcased in Pineapple Express. Produced by the ever-prolific Judd Apatow, this action-comedy intertwines humor with an exhilarating plot revolving around a group of friends who indulge in recreational substances. It’s a film that captures the zeitgeist of its time.

With Seth Rogen portraying his quintessential lovable loser character alongside James Franco and Gary Cole, it encapsulates the humor of the millennial generation. The film enjoyed commercial success with over $100 million at the box office and holds a respectable 68% rating on Rotten Tomatoes, reflecting its enduring appeal.

8 The 40-Year-Old Virgin

Directed by Judd Apatow

In The 40-Year-Old Virgin, Judd Apatow brilliantly blends humor with heart in a story that centers on Steve Carell’s breakout role as a shy, inexperienced salesman navigating the complex world of dating. With an ensemble cast that includes Seth Rogen and Paul Rudd, the film strikes a balance between hilarious antics—like the unforgettable waxing scene—and genuine moments of romance.

Garnering over $100 million in U. S.grosses alone, the film is notable for its wit and emotional resonance, achieving an 85% score on Rotten Tomatoes, a nod to its widespread acclaim among both audiences and critics.

7 Juno (2007)

Directed by Jason Reitman

Juno features a sharp, witty protagonist navigating the challenges of teenage pregnancy with an endearing mix of humor and poignancy. Elliot Page delivers a memorable performance, supported by a stellar cast, including Jennifer Garner and J. K.Simmons. The film’s exceptional script, penned by Diablo Cody, earned an Academy Award, alongside three additional nominations.

With a modest budget of around $7 million, Juno achieved box office success, grossing over $230 million globally. Its 93% Rotten Tomatoes score underscores the film’s impact, and its cultural relevance continues to be felt, recently referenced in pop culture.

6 I Love You, Man

Directed by John Hamburg

This fresh take on the romantic comedy genre focuses on male friendship as Paul Rudd’s character, facing an impending wedding, realizes he lacks close male bonds. The relatable premise resonates in today’s technology-driven world, making the film’s themes timeless.

The delightful dynamic between Rudd and his co-star is palpable, while a talented supporting cast, including JK Simmons and Andy Samberg, enhances the film’s humor. Memorable one-liners, like “See you later, Jobin, ”contribute to its enduring charm, supported by an 82% rating on Rotten Tomatoes.

5 Miss Congeniality

Directed by Donald Petrie

Miss Congeniality revitalized Sandra Bullock’s career and solidified her as a comedic force in the new decade. Although it plays into the classic trope of an undercover agent blending into a beauty pageant, Bullock’s portrayal of an awkward yet charming character anchors the film amidst thrilling action and mystery.

Supported by notable performances from Michael Caine and Candace Bergen, the film’s engaging makeover sequence remains iconic. With over $200 million in global box office receipts, it has achieved a lasting legacy, including a sequel that continues to capture audience interest.

4 Anchorman: The Legend of Ron Burgundy

Directed by Adam McKay

Will Ferrell shines in his role as Ron Burgundy, a caricature of a pompous news anchor. This film, packed with memorable moments—including a spontaneous street fight and comical jazz flute solo—showcases Ferrell’s comedic prowess and the exceptional ensemble cast’s talents.

The film’s influence is evident, as it became a defining work of the era and established Ferrell as a comedy heavyweight. Its legacy continued with a sequel, further exploring the beloved characters while introducing fresh comedic talent.

3 Forgetting Sarah Marshall

Directed by Nicholas Stoller

A hallmark of the romantic comedy genre, Forgetting Sarah Marshall masterfully blends humor with a heartfelt narrative. Jason Segel’s character, Peter, finds himself in hilariously vulnerable situations after an unexpected vacation meeting with his ex and her new partner. His comedic portrayal of awkwardness—acompanied by a hilarious Dracula musical performance—shows a depth beyond mere laughs.

The film thrives with a strong supporting cast, including Paul Rudd and Jonah Hill, and boasts scenic Hawaiian landscapes that augment its charm. Grossing over $100 million with an 82% Rotten Tomatoes rating, it illustrates a successful union of comedy and emotional storytelling.

2 Legally Blonde

Directed by Robert Luketic

Elle Woods, portrayed by Reese Witherspoon, is an empowering figure who challenges stereotypes about women in academia. Her spirited journey from a seemingly superficial sorority girl to a determined law student embodies the film’s underlying message of perseverance and self-belief. The laughter peppered throughout the film reinforces its uplifting themes.

Highlighting elements of friendship and empowerment, Legally Blonde made nearly $150 million globally and is celebrated for its quotable moments and humor. Even now, it continues to inspire a new generation with an anticipated prequel currently in development.

1 Little Miss Sunshine

Directed by Jonathan Dayton and Valerie Faris

Little Miss Sunshine stands as a unique entry in the comedy genre, prioritizing heartfelt storytelling over flashy humor. The film chronicles a dysfunctional family’s road trip to a child beauty pageant, illustrating both mundane and profound moments of connection among its cast, including Toni Collette and Alan Arkin.

With Abigail Breslin in a breakout role, the family’s journey through mishaps offers laughter intertwined with poignant moments. Critics lauded its emotional depth, leading to two Academy Awards and a 91% rating on Rotten Tomatoes, ensuring its status as a beloved classic that continues to resonate with audiences.

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