The news that Judd Apatow will co-write and direct an upcoming 2027 comedy movie,* The Comeback King*, with Glen Powell 20 years after Knocked Up proves that the long-awaited return of a beloved Hollywood era is finally coming. When ‘00s comedy movies are mentioned, one name looms large over this period of the genre’s history. Writer/ director/ producer Judd Apatow produced Will Ferrell classics like Anchorman: The Legend of Ron Burgundy,* Talladega Nights: The Ballad of Ricky Bobby*, and Stepbrothers, directed the influential bromance comedies* The 40-Year-Old Virgin and Knocked Up*, and had a hand in almost every iconic comedy of the decade.
From 2005 until around 2015, comedy fans couldn’t go to the cinema without spotting another hit from Apatow and his regular rotation of collaborators, including Paul Rudd, Seth Rogen, Jonah Hill, Danny McBride, and Apatow’s real-life wife, Leslie Mann. However, while this era also kick-started the career of Hollywood comedy legend Adam McKay, thanks to his production of McKay’s early movies, Apatow’s reign as Hollywood’s king of comedy couldn’t last forever.
In 2027, Glen Powell will star as a country musician who is struggling with his career’s disastrous failure in Apatow’s aptly-named comedy movie The Comeback King. With a stacked ensemble cast that includes Cristin Milioti, Stavros Halkias, Madelyn Cline, and Jin Hao Li, the movie could be a major comeback for Powell after the box office failure of his dystopian Stephen King adaptation, The Running Man. However, the movie’s real appeal is its chance to bring Apatow and his unique brand of comedy back to mainstream acclaim.
2027’s upcoming Powell vehicle could not be more appropriately titled, since The Comeback King marks Apatow’s first directorial effort since 2022’s disastrous flop, The Bubble. To be fair to that star-studded misfire,* The Bubble* was one of the earliest attempts to make sense of the COVID-19 pandemic through the medium of Hollywood comedy, and not every effort at this admirable goal could be as epochal as Bo Burnham’s deservedly acclaimed Inside.
That said, the failure of *The Bubble *wasn’t the first flop for Apatow, but rather the last in a string of failures that gradually proved his style of comedy was falling out of favor with viewers. Apatow and Rogen’s $220 million “Bromance” Knocked Up was a massive critical and commercial success in 2007 and proved, after The 40-Year-Old Virgin’s $177 million box office payday two years earlier, that R-rated comedy was a force to be reckoned with at the box office.
Knocked Up went on to influence countless comedies about man-children behaving badly throughout the late 2000s and early 2010s, but this trend died out way sooner than a lot of viewers may remember. The Hangover trilogy started out strong in 2009, but ended with a critically derided whimper only four years later in 2013. Similarly, Rogen’s sophomore directorial effort,* The Interview*, flopped as early as 2014, while 2011’s expensive Danny McBride vehicle, Your Highness, proved that stoner comedies didn’t mix with high fantasy as successfully as they had with action thrillers in Pineapple Express three years earlier.
Apatow’s career started way back in the early ‘90s, but he wouldn’t become a major presence in Hollywood until the mid-2000s. While Anchorman: The Legend of Ron Burgundy and The 40-Year-Old Virgin were breakout hits for stars Steve Carell and Paul Rudd, it was the one-two punch of Knocked Up and Superbad that caused Hollywood to truly sit up and take notice. The two 2007 movies came out within a few months of each other and were massive sleeper hits at the box office, not despite, but because of their foul-mouthed, strictly R-rated humor.
2008 saw Apatow produce Pineapple Express,* Forgetting Sarah Marshall*, and Stepbrothers in quick succession, but the first cracks in his once-reliable formula started to appear as early as 2009’s* Funny People*. This ambitious dramedy featured a great central performance by Adam Sandler, but its lengthy runtime put off many viewers and, despite solid reviews, Funny People failed to earn back its $75 million budget.
By 2012, the middling reception of *This Is 40 *slowed things down further for Apatow, while the emergence of indie comedy directors was making his brand of offbeat dramedy less of a niche offering. The works of Apatow protégé Lena Dunham, Sean Baker, Jesse Peretz, Leslye Headland, and future blockbuster director Greta Gerwig all meant that Apatow’s success had given rise to an entire low-budget dramedy subgenre that flourished on streaming instead of in cinemas.
While Apatow enjoyed some box office successes during this era, like 2011’s Bridesmaids, 2015’s Trainwreck, and 2017’s The Big Sick, the super producer also weathered some of the biggest flops of his career. The financial failure of 2016’s *Popstar: Never Stop Never Stopping *was one such misstep, as was the underperformance of 2012’s The Five-Year Engagement and the 2020 failure of The King of Staten Island. When 2022’s Bros underperformed, it was clear the bromance sub-genre Apatow shaped with his early movies had fallen out of fashion.
Outside of Apatow’s projects, the box office failure and critical dismissal of both 2012’s That’s My Boy and 2015’s Hot Tub Time Machine 2 proved that bromances were on the decline everywhere. Meanwhile, major flops like 2018’s Holmes and Watson soon meant that major studio comedies became an increasingly rare sight at the multiplex. Rogen pivoted to streaming projects, producing huge Prime Video hits like* The Boys *and Invincible, while Apatow spent the 2020s mostly focused on documentaries like Stormy,* You Had to Be There*, and Paralyzed by Hope: The Maria Bamford Story.
Every Judd Apatow Movie Ranked From Worst To Best (Including The Bubble) ](/judd-apatow-movies-ranked-worst-best/)
The Bubble’s director has had a long and impactful film career. Here are all of Judd Apatow’s movies ranked from the worst to the best.
Fortunately for* The Comeback King*’s prospects, Apatow’s comedy stylings have enjoyed something of a resurgence in recent years. If TikTok trends and the resurgence of mid-budget ‘00s comedies on streaming are anything to go by, a cohort of Gen Z viewers is nostalgic for the Superbad/ The Hangover/ Hot Tub Time Machine era of late ’00s bromance comedy, and The Comeback King could be just the thing to bring comedy back into the multiplex in a big way. It’s a big ask, but if anyone can revive Hollywood comedy’s mid-00s Golden Age, it is its original hitmaker, Knocked Up** director Judd Apatow.
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