From Hilarious to Heartwarming: The Best 2000s Will Ferrell Films

Will Ferrell
Everett Collection

Will Ferrell turns 56 today and I have the honor of writing about some of his funniest movies (and a few of my personal favorites) as a big fan. Many of my favorite movies premiered in the 2000s when I was a teenager, so a heavy dose of nostalgia plays a role in my appreciation for the SNL star. Of course, like any actor, he’s had some incredible success and some flops over the years, but he has proved that he is a force to be reckoned with as an actor and comedian. Let’s just promise not to discuss his guest-starring role in The Office (I had such high hopes for my favorite actor in one of my favorite shows and it was just… bad.) However, feel free to comment and let me know which movies you love, hate, or think I missed from this list!

Zoolander (2001)

ZOOLANDER, Will Ferrell, 2001

Paramount/Everett Collection

Ferrell usually plays the hero or at least the redeemable main character in films so it was a surprise to see him as an over-the-top villain. As Mugatu, he really went for it and embraced the evil, yet wacky character always carrying around a little dog that looks a little too much like his wig. Of course, Derek Zoolander (Ben Stiller) defeats him in the end, and rightfully so, but I still love any scene with Mugatu. You can watch it on Hulu.

Old School (2003)

OLD SCHOOL, Jeremy Piven, Vince Vaughn, Luke Wilson, Will Ferrell, 2003

DreamWorks/Everett Collection

As Frank the Tank, this is perhaps one of Ferrell’s most memorable characters (besides “More Cowbell!”). He starts a fraternity with old pals Mitch (Luke Wilson) and Beanie (Vince Vaughn). This might be one of the first of many “bro comedies” and the streaking scene is unforgettable. You can watch it on Paramount+.

Elf (2003)

ELF, Will Ferrell, 2003

New Line/Everett Collection

Elf is one of the most beloved Christmas films but Ferrell has dashed many dreams as he has said there will never be a sequel. Starring as Buddy the Elf, he leaves the North Pole in order to find his real dad and doesn’t fit in in New York City as well as he hoped. But, it has a sweet, happy ending and the film is full of feel-good laughs that will make you want to re-watch it every holiday season. You can watch it on Amazon Prime Video.

Anchorman: The Legend of Ron Burgundy (2004)


Dreamworks/Everett Collection

Critics didn’t like this one as much as the audience did but it has become one of his most notable films to date and spawned a pretty good sequel several years later. Ferrell plays Ron Burgundy and the film is full of some of his best one-liners. This is one of the first Ferrell films I saw and is definitely one of my favorites of all time. You can’t go wrong with the cast, especially when Ron and Veronica Corningstone (Christina Applegate) hurl silly insults at each other. You can watch it on Paramount+.

Talladega Nights: The Ballad of Ricky Bobby (2006)

Talladega Nights The Ballad of Ricky bobby

Everett Collection

“If you ain’t first, you’re last.” Ferrell’s films are usually over the top, at times a little cringy, yet hilarious. Ferrell stars as Ricky Bobby, obsessed with NASCAR, and finally gets a chance to prove his skills. He quickly turns into an egotistical maniac that eventually experiences a downfall and finds out what truly matters. “Shake and bake!” You can watch it on Freevee.

Stranger Than Fiction (2006)


Sony Pictures/Everett Collection

Perhaps this is a controversial choice because it isn’t one of his funniest, but I loved it because it was so different from many of his other films. Ferrell plays Harold Crick, an IRS agent who loves a routine. However, he finds out that he is a character in a book and the writer always kills off her protagonists. So, he is on a quest to convince her to keep him around as he’s fallen in love with a woman who has changed his life. It is not as laugh-out-loud funny, but it will pull at your heartstrings.

Step Brothers (2008)

STEP BROTHERS, from left: Will Ferrell, John C. Reilly, 2008

Columbia Pictures/Everett Collection

You have to give it to Ferrell and the entire cast for this one. While it wasn’t as well-received at first, it has become a comedic classic that helped to secure Ferrell and John C. Reilly as a duo you can’t help but laugh at. As two 40-year-olds living with their single parents, they are forced to live together when their parents get married. After hating each other at first, they end up becoming best friends and their fight scenes are some of the best, and of course, the film has plenty of quotable lines. You can watch it on Hulu.

The Other Guys (2010)

THE OTHER GUYS, from left: Will Ferrell, Mark Wahlberg, 2010

Macall B. Polay/Columbia Pictures/Everett Collection

Ferrell works well with Mark Wahlberg in a story about an unlikely duo of a cop and a forensic accountant. One of my favorite scenes is a flashback showing that Ferrell’s Allen Gamble wasn’t always the mild-mannered accountant as he had a past as a pimp and always attracts beautiful ladies, including his wife Shiela (Eva Mendes). It is one of his top films based on critic reviews and I’d have to agree it is one of the funniest. You can watch it on Amazon Prime Video.

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March 2021

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