Looking at Comedy in the 21st Century

Orrin Konheim
7 min readDec 7, 2020

At the start of the 21st Century, The box office for comedies was dominated by a handful of stars. Look at this list of weekend winners from 1999 through approximately 2003 and you’ll see roughly the same list of headliners leading comedy films: Jim Carrey (Liar, Liar, How the Grinch Stole Christmas, Bruce Almighty), Mike Myers (Austin Powers II and III, Cat in the Hat, Shrek), Will Ferrell (Night at the Roxbury, Elf, Old School), Adam Sandler (Big Daddy, Me Myself and Irene, Mr Deeds, Anger Management), Julia Roberts (Runaway Bride, Mona Lisa Smile), Will Smith (Wild Wild West, Men in Black II, later Hitch), and Sandra Bullock (Forces of Nature, Miss

Starting around 2003, the term “Frat Pack” was coined for a group of actors — Ben Stiller, Jack Black, Owen Wilson, Vince Vaughn, Luke Wilson and Will Ferrell — who would often take roles in each other’s movies. Like Frank Sanatra’s original Rat Pack, they became a collection of symbiotic brands voicing their own distinct personalities and each capable of headlining their own film. Luke Wilson was arguably more of a straight man and it seems baffling in retrospect that he would get his own films, but think a poor man’s Jason Bateman (maybe nepotism?).

The next big development was Judd Apatow who bought his own troupe — Seth Rogen, Jonah Hill, James Franco, Michael Cera, Jay Baruchel, Jason Segel — some from his failed television show “Freaks and Geeks” and further popularized a brand of R-rated comedies starring stoner man children (though I’d argue that the non-Apatow product, the Wedding Crashers was the start of the trend):

The unrealistic romantic fantasies of the Apatow aesthetic are mocked in this video:

Apatow was also a producer and encouraged a number of his stars to create their own projects through writing them to the point where Seth Rogen became a director of his own alongside Greg Mottola in movies that were stylistically similar to Apatow’s products. Apatow would later go in other directions which we will get to next decade.

Other comedic forces included Tina Fey (Mean Girls) and Adam McKay (Anchorman, Talladega Nights, Step Brothers) who were both head writers of Saturday Night Live at various points…

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Orrin Konheim

Freelance journalist w/professional bylines in 3 dozen publications, writing coach, google me. Patreon: http://www.patreon/com/okjournalist Twitter: okonh0wp