While director Adam McKay and star Steve Carell have collaborated four times, their movie projects could not be more different. McKay first directed Carell in 2004’s comedy cult classic Anchorman: The Legend of Ron Burgundy. Although the movie was a star vehicle for Will Ferrell, Anchorman proved a huge success for Carell as well. While Ferrell was already a comedy A-lister thanks to 2003’s Elf, Carell’s hysterical ing character Brick Tamland made him Anchorman's breakout star. This role, alongside 2005’s The Forty-Year-Old Virgin, cemented Carell’s status as a comedy superstar. McKay and Carell wouldn’t collaborate again until 2013’s Anchorman 2: The Legend Continues.

After that, 2015’s real-life satire The Big Short was a major tonal shift for the duo. This dark comedy took a look at 2008's housing market collapse. Carell played Mark Baum, the leader of an independent trading firm who was among the first traders to realize that the subprime mortgage bubble was ready to burst. The Big Short proved that McKay and Carell could make heavier, darker subjects funny, leading to 2019’s Dick Cheney biopic Vice. This grimly funny movie saw Carell play Donald Rumsfeld, one of the architects of the Iraq war. Carell’s Rumsfeld was frequently chilling but also provided a surprising number of bleak laughs.

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4 Anchorman 2: The Legend Continues

Brick and Chani drink soda together in Anchorman 2

2013’s Anchorman 2: The Legend Continues is an inessential sequel, but the movie’s wild finale justifies its existence. While it isn’t Adam McKay and Will Ferrell’s funniest movie, Anchorman 2 does manage to bring back the wild, freewheeling comedic energy of the original movie almost a decade later. Carell’s Brick remains a scene-stealing highlight, while Kristen Wiig is hilarious as his love interest Chani Lastnamé. Meanwhile, the satire of modern news cycles works well. A disted narrative and lengthy runtime mean that Anchorman 2: The Legend Continues might be the weakest of the pair’s collaborations, but this fun follow-up is very much the worst of a great bunch of movies.

3 The Big Short

Mark Baum (Steve Carell) looks annoyed in The Big Short

2015’s The Big Short irably manages the unenviable task of condensing the 2008 housing crisis into digestible blockbuster form. A stacked ing cast including Brad Pitt, Ryan Gosling, Christian Bale, and Succession’s Jeremy Strong ensure that The Big Short’s mission is a success, despite some tonal wobbles. Like McKay’s later satire Don’t Look Up, The Big Short is occasionally too righteously angry to feel loose and funny, and at other points too playfully arch to feel appropriately impactful and intense. However, The Big Short’s scathing economic history lesson is still sharp, witty, and essential viewing despite the movie's occasional tonal inconsistencies.

2 Vice

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After The Big Short proved Christian Bale and McKay were a formidable pairing, 2019’s Vice attempted an even more ambitious tonal balancing act. A sharp back on a dark chapter of American history, Vice is a brutally brilliant watch. Bale’s grouchy, sneering Cheney manages to humanize the war criminal without excusing his actions, while Carell is on typically stellar form as Rumsfeld. One scene sees a scheming Rumsfeld excitedly inform Cheney about Kissinger’s bombing of Cambodia. Not all of Vice’s uneven runtime can capture this moment’s existential horror but, in this instant. Carell and McKay manage to put a grinning human face on the horrors of American imperialism.

1 Anchorman

Steve Carell laughing as Brick in Anchorman

2004’s Anchorman is an anarchic, goofy comedy filled with inspired characters and absurd set-pieces. However, underneath all the comical hairpieces and absurd quotes, McKay also subtly satirized the media industry’s sexism. Christina Applegate is superb as Ferrell’s beleaguered new colleague, while Will Ferrell gives one of his funniest turns ever as Ron Burgundy. A walking embodiment of 70s machismo and transparent insecurity, Ron Burgundy is an all-time great comic creation. However, he is only as funny as his co-stars and, even in a movie that features some of the funniest line-readings of Paul Rudd and David Koechner’s careers, Carell kills in this department with a star-making ing turn.

The naive, oblivious Brick might be a hapless fool, but he has a heart of gold that makes Carell’s character irresistible. As much as Anchorman was a star vehicle for Ferrell, the movie also functioned as an introduction to the brand of blithe, blissfully unaware goofball Carell made his own in the years that followed. Will Ferrell and Steve Carell’s collaboration here was as charming and funny as anything that Ferrell made with John C. Reilly later, while Carell planted the seeds of The Office’s Michael Scott in Brick’s innocent blundering. While Adam McKay and Steve Carell have since made more serious movies, Anchorman remains their strongest effort.