'A Night At The Roxbury' (1998)
We can't really say he made the big leap from the small screen to the silver screen in this film, considering it was based on an 'SNL' skit that was already on borrowed time before the feature-length even came out. We can at least credit him with exceptional head-bopping skills, something that must have pushed the actor to his physical limits now having to do it for a 82 minutes rather than five on late night TV. 'A Night At The Roxbury' has gone on to be a cult classic, which is a euphemism for "so bad it's good," (though we feel only one-half of that euphemism is accurate).
Ferrell stole every scene he was in as Mugatu, the fashion designer who hires a male model to unwittingly assassinate the president of Malaysia (yeah, THAT tired trope!). We shudder at the thought of what Andy Dick, whom the role was originally written for, would have brought -- or taken away -- from the film.
The less said about the sequel, the better.
'Old School' (2003)
Will traded Owen Wilson for brother Luke in this frat boy comedy that's low on original story but high on laughs. It demonstrated two things: (i) Ferrell's dedication to comedy, as he was actually naked for his streaking scene, and (ii) he can bring an otherwise bland line to life with ease. "We're going streaking!" and "You're my boy, Blue"... Dame Judi Dench could not have delivered those lines with more aplomb.
The film that shot Will Ferrell to cinematic stardom may also be his best. Will plays Buddy, a regular (read: very tall) fellow who, after being raised as an elf in Santa's Village, seeks out his biological father in the Big Apple. With supporting roles by James Caan, Mary Steenburgen, Zooey Deschanel, and Bob Newhart, you know you're in good hands.
Another film whose claim as Will Ferrell's best is a tough one to oppose. A stellar cast including Christina Applegate, Steve Carell, Paul Rudd, and David Koechner make for one hilarious movie with sooo many quotable lines. In fact, you could be forgiven for resenting the movie in light of all the Ron Burgundy impressions it inspired in its wake.
The less said about the sequel the better.
'Wedding Crashers' (2005)
We know Will is only in two scenes but Alec Baldwin was in 'Glengarry Glen Ross' for one scene and he won an Oscar.
Besides, his unforeseen cameo as Chazz, the ur-wedding crasher and all-round despicable person, reignites the humour in the film's second act and saves it from becoming some male-centric melodrama. And no one wanted that.
'Talladega Nights: The Ballad of Ricky Bobby' (2006)
Taking place in the weird and incomprehensible world of NASCAR is this spiritual sequel to 'Anchorman' in which Ferrell plays an ignorant narcissist who is first on top, then is down and out, then must learn to value his partner/friend/co-anchor to be on top again.
The anything-for-a-laugh Ferrell had one of his richest roles in the absurdist fantasy 'Stranger Than Fiction' (2006). He played a humourless accountant who becomes the inadvertent subject of a novelist's latest book. He shined best in his romantic moments with tax-ignoring baker Maggie Gyllenhaal. The scene where he seduces her by singing the Wreckless Eric song 'Whole Wide World' is priceless.
'Blades Of Glory' (2007)
Evidently Ferrell thinks the name 'Chazz' is funny. And he wouldn't be wrong. He plays another one (see: 'Wedding Crashers') in 'Blades Of Glory', a film about a pair of shamed male figure skaters who partner in order to realize their dreams of winning gold. Ferrell plays the sexist and egotistical one of the "let's overcome our differences for a common goal" pair, apparently improvising or altering a vast majority of his lines. The directors knew better than to interfere, as Chazz delivers the film's best lines.
'Step Brothers' (2008)
In 2008, Ferrell and 'Talladega Nights' co-star John C. Reilly reunited for another movie in which Ferrell plays a manchild. When you have a schtick, you have to stick, right? Sort of a "Brady Bunch Of Delinquents", with both featuring blended families and kids who think they're musically inclined. Also features Mary Steenburgen who brings the eye candy as Ferrell's mother, Nancy, despite being only 14 years older than her on-screen son. Its movie poster continues the trend set by 'The 40-Year-Old Virgin' in which the star stares wondrously at the top-left-hand corner beneath a Glamour Shots sheen.
'The Other Guys' (2010)
Yet another Adam McKay joint (these guys really, REALLY like working with each other). This time Ferrell teams up with Mark Wahlberg to play the titular roles -- two black-sheep cops who must work together to catch the bad guy or save the city or something. The film wouldn't be the last time Ferrell and Wahlberg play off each other on screen.
One helluva cast (of voices), which includes Brad Pitt, Jonah Hill, Tina Fey, and David Cross, speak alongside Ferrell as he brings life to Megamind, a baddie who becomes a goodie (like another CGI feature that came out in 2010. That also featured a character called 'minion'). Ferrell cut his teeth playing the voice of an animated villain, a skill set that would serve him well on a bigger stage built of Lego several years later.
'The Lego Movie' (2014)
What some predicted as being nothing more than a 90-minute commercial was something of a Cinderella story, with critics and fans hailing the film from Phil Lord and Chris Miller as clever and touching. The 'touching' bit comes courtesy of the film's meta-ending, starring a real-life Ferrell (who also voiced Lord Business) in a G-rated scene that tied the whole film together (that's the 'clever' bit).
'A Deadly Adoption' (2015)
When news of this Lifetime movie starring Will Ferrell and Kristen Wiig first leaked out on April 1, 2015, many assumed the whole thing was an April Fool's joke. Wrong! 'A Deadly Adoption' is for real, and finds the 'SNL' alums in the inspired-by-a-true-story "high-stakes dramatic thriller" about a couple who invite a pregnant woman into their home with hopes of adopting her unborn child. Though it was seemingly intended as a parody of the "Lifetime TV movie" genre, "Adoption" was played a bit too straight for many viewers who couldn't tell whether it was a send-up or an earnest Lifetime drama.