Will Ferrell is widely known as one of the greatest comedic actors of the last 40 years. Since his beginnings in the mid-1990s as a cast member of Saturday Night Live, Ferrell’s been gifting audiences with some of the funniest and most unforgettable performances on both the small and big screen. Some of his most legendary roles include the iconic fashion villain Jacobim Mugatu with his Flock of Seagulls-styled hairdo, and the smooth-talking mustachioed newsman Ron Burgundy.

While Ferrell’s had hits in every decade since the 1990s, it’s no secret that the height of his onscreen career was in the 2000s with a string of comedy hits that solidified his reputation as a top-tier performer. Ferrell’s natural goofiness and his knack for playing characters who take themselves seriously despite their undeniable absurdity was on full display during this period. From minor roles like his portrayal of jealous husband Lance DeLune in The Ladies Man to Detective Allan Gamble in The Other Guys, this is the definitive ranking of Ferrell’s films from the 2000s.

18

‘The Ladies Man’ (2000)

Directed by Reginald Hudlin

The Ladies Man is a 2000 sex comedy film based on the 1990s SNL skit starring Tim Meadows. Meadows plays the titular ladies’ man, Leon Phelps, a young, smooth-talking player who hosts a program where he offers listeners questionable dating advice. After getting sacked for taking his show a little far, Leon receives a letter from a former flame with no name attached and proceeds to go on a journey to find her while also being tailed by a secret group of angry husbands who want revenge on Leon for sleeping with their wives.

Ferrell plays the antagonist and leader of the Victims of the Smiling Ass, Lance Delune. Ferrell plays his character with seething anger and comical homoerotic overtones. He pivots, in typical Ferrell fashion, from loud and commanding to tentative and coy. It’s not one of his best roles, and it’s far from the best film on the list, but it’s still a fun watch nonetheless.

17

‘Drowning Mona’ (2000)

Directed by Nick Gomez

Drowning Mona is a 2000 crime comedy film that stars Danny DeVito as police chief Wyatt Rash, who investigates the death of Mona Dearly (Bette Midler), a vindictive, hard-boozing, abusive woman detested by everyone and their mother. This hidden comedy gem also stars William Fichtner as Mona’s abused husband, Jamie Lee Curtis as Rona, a waitress he has an affair with, and Casey Affleck as a dim-witted gardener.

In Drowning Mona Ferrell plays Cubby, the wide-eyed, off-putting funeral director. While he doesn’t have a considerable number of lines in the film, Ferrell plays his character with the utmost weirdness, making worthwhile what little screen time he does have. The ensemble cast (which includes DeVito in one of his funniest movies) of Drowning Mona give over-the-top absurd performances in this highly underrated black comedy.

16

‘The Wendell Baker Story’ (2005)

Directed by Andrew Wilson and Luke Wilson

Andrew and Luke Wilson’s The Wendell Baker Story is a little-known passion project by the two brothers that follows the story of Wendell Baker (Luke Wilson), an ex-con who works at a retirement home and hopes to win back the heart of his former flame, Doreen (Eva Mendes). The supporting cast of the film also includes Harry Dean Stanton and Kris Kristofferson.

The Wendell Baker Story is a funny film that doesn’t get as much love as it should. Wilson kills it in his role as the good-hearted, but trouble-prone Wendell Baker, and Ferrell does an outstanding job as the memorable grocery store manager. Ferrell’s probably at his best when he plays characters that are quick to anger, and watching him slug Wilson in the face is a scene that never gets old.

15

‘Semi-Pro’ (2008)

Directed by Kent Alterman

Semi-Pro is Kent Alterman‘s directorial debut, and it stars Ferrell as fictional singer turned basketball player Jackie Moon. In 1976, Jackie uses the cash from his only hit-single to own a basketball team, but unfortunately for Jackie, his team is the worst in the league. When the NBA and ABA announce plans to merge, it’s up to Jackie and his middling players to ball their way to survival.

Despite being panned by critics, Semi-Pro is actually pretty funny. Chances are if you like comedy that’s shamelessly ridiculous, then you’ll appreciate it. It’s a hilariously unserious film that’s not unlike many of the projects Ferrell’s known for. While he gives a hysterical performance as Jackie Moon, who he portrays as an absolute buffoon, co-stars Woody Harrelson as an aging point guard and Will Arnett as the cigarette-smoking, hard-boozing commentator are also noteworthy.

Semi-Pro

Release Date

February 28, 2008

Runtime

91 minutes

14

‘Kicking & Screaming’ (2004)

Directed by Jesse Dylan

Kicking & Screaming is a sports comedy film that depicts the struggle between a father and son who coach opposing soccer teams. Phil is the proprietor of a vitamin shop and a regular guy who endured a traumatic upbringing by his competitive and ruthless father, Buck (Robert Duvall). When Phil’s son is dismissed from Buck’s soccer team, Phil takes it upon himself to coach his son’s new team and challenges Buck and his soccer team.

Screaming & Kicking is a fun family film that features Ferrell as a soccer dad that’s completely off his rocker. Ferrell is at his absolute best in performances where he gets to yell and really lean into the physicality of his character, and in Kicking & Screaming, his outbursts and unhinged wildness are at the top of their game. With Mike Ditka and Robert Duvall as his co-stars, Screaming & Kicking makes for a fun and silly sports film.

13

‘Land of the Lost’ (2009)

Directed by Brad Silberling

Land of the Lost is a 2009 science fiction adventure comedy film that’s loosely based on the Sid and Marty Krofft television series of the same name. Land of the Lost follows scientist Rick Marshall (Ferrell), his assistant Holly Cantrell (Anna Friel), and survivalist Will Stanton (Danny McBride), who get sucked into a space-time vortex and find themselves in a strange world with dinosaurs and bizarre creatures called Sleestaks.

In Land of the Lost, Ferrell plays a character that’s notably more understated than the roles he’s known for, but he still brings his unique comedic flair to the performance. While Land of the Lost has plenty of crude jokes and outrageous scenes, it’s also got heart. For fans of McBride, who just wrapped up the final season of The Righteous Gemstones, Land of the Lost is an excellent film to watch if you want to catch these two comedy geniuses collaborating together.

12

‘Jay and Silent Bob Strike Back’ (2001)

Directed by Kevin Smith

Jay and Silent Bob Strike Back is a 2001 comedy stoner film that follows the eponymous characters on a journey to sabotage a movie based on their comic book counterparts after discovering that they won’t be cashing in on any royalties. Jay and Silent Bob Strike Back features an ensemble cast filled to the brim with appearances from a slew of stars, including Carrie Fisher, Wes Craven, and Alanis Morissette.

The 2000s were one of the greatest decades for comedy films. One of the defining characteristics of the era was that you could find yourself watching one of the silliest comedy films and be shocked by the number of recognizable stars who would appear as part of the cast. Jay and Silent Bob Strike Back are a perfect example of this. It’s got George Carlin playing a hitchhiker, Matt Damon popping in for a cameo, and even Mark Hamill makes an appearance. Jay and Silent Bob Strike Back is a hysterical film that’s got plenty of crude humor and zany antics, and it features Ferrell in a hilarious role as the do-good Federal Wildlife Marshal Willenholly.

11

‘Melinda and Melinda’ (2004)

Directed by Woody Allen

Woody Allen‘s Melinda and Melinda is a comedy romance film that stars Wallace Shawn, as Sy, a man at dinner with friend who contemplates the difficulty between separating tragedy and comedy. To illustrate his point, Sy tells the story of two different Melindas (Radha Mitchell) who both cope with a recent divorce by abusing substances and also starting to begin a complicated relationship with a close friend of their ex-husband.

Allen’s one of the greatest blenders of comedy and drama, and with Melinda and Melinda he shows audiences exactly why that is. Ferrell stars as Hobie, a failed actor who falls for Melinda and develops a friendship with her. Ferrell imbues his role with the hilarious awkwardness of the characters Allen typically features in his films, and a uniquely humanizing warmth that’s different from the roles we’re used to seeing him in. Melinda and Melinda is another great film by Allen that boasts strong performances from Chloë Sevigny and Steve Carell.

10

‘The Producers’ (2005)

Directed by Mel Brooks

Comedy legend Mel Brooks directed a remake of The Producers in 2005, a musical comedy that starred Matthew Broderick and Nathan Lane as shameless producers who try to scam a group of elderly ladies by persuading them to invest in what’s projected to be an awful Nazi-themed musical. Ferrell stars as the former Nazi whose musical, “Springtime for Hitler”, is picked up by the conniving producers.

Though the modern film adaption of The Producers is arguably not as good as its predecessors, Brooks manages to give audiences a hysterically funny movie nonetheless. Broderick and Lane are brilliantly cast as the two plotting producers, and Ferrell gives one of his most gut-bustingly funny performances as the overcharged former Nazi. His German accent is completely ridiculous, but that’s also kind of the point. Though The Producers is a bit uneven at times, it has sidesplitting performances and excellent musical numbers that revel in their absurdity.

The Producers

Release Date

December 25, 2005

Runtime

134 minutes

9

‘Blades of Glory’ (2007)

Directed by Will Speck and Josh Gordon

Will Speck and Josh Gordon‘s Blades of Glory follows the story of two banned figure skaters (Ferrell and Jon Heder) who discover a loophole that allows them to compete again. Blades of Glory was developed from an original story by Busy Philipps, who conceived of the idea while watching television with her visiting boyfriend. It also featured Arnett and Amy Poehler.

Blades of Glory features Ferrell in one of his best performances, playing Chazz Michael Michaels, an arrogant egomaniac and sex addict opposite Heder, who plays a softer, more timid character. The chemistry between the two characters, who find themselves competing in pairs so they can reenter the figure skating world, is undeniably good. It’s ridiculously over-the-top, like any good Ferrell film, and it’s got stellar supporting performances from Poehler, Arnett, and Jenna Fischer.