Ones on 1 is a monthly feature in which I write about a selected film that reached number one at the box office for precisely one weekend. This month, we examine the film that took the crown on August 2, 2009: Funny People.

Five years removed from its theatrical run, it seems particularly insane that a film like Judd Apatow’s Funny People was given a wide release. It’s hard to even recall a recent independent movie that has aimed for the same kind of specific, rambling ambition. There may not be another movie like it, and that is both to its credit and detriment. It isn’t terribly unique on a micro level, but when looking at the big picture—and all the bits, conflicts and ideas it throws into its 146-minute stew—it reveals just how strange and admirable this whole undertaking was. This could only be made by someone who had already reached the top of the mountain, and by the time Funny People came out, Apatow was on an unparalleled roll. This film ended that roll, but it clearly wasn’t for lack of trying.

Apatow may have spent the better part of the ’00s slapping his name on project after project, but when he actually steps behind the camera to direct, he seems incapable of making something impersonal. His films are often loaded with autobiographical details, including a penchant for casting his daughters Maude and Iris Apatow, and having them play prominent roles in his ensembles. He also, increasingly, wants his films to be about things, even if said things don’t always turn out to be that relatable. (This is particularly where This is 40 ran into trouble.) As interesting as the subject of Funny People may occasionally be, there aren’t many people in this world that can identify with the struggles of a multimillionaire comedian/movie star. Relatability isn’t necessary for a subject to be interesting, of course—movies normally aren’t about people we would meet in everyday life. This just becomes a problem whenever Apatow strives for universality, such as in Funny People’s second half.

The first half, however, often sees Apatow at the peak of his powers. He’s able to get a career-best performance out of Adam Sandler as George Simmons, a nasty, lonely movie star who has made a living starring in films not unlike Sandler’s own oeuvre. (The cinematic output is more or less where the comparisons end, considering Sandler is by all accounts a perfectly decent family man.) After receiving a leukemia diagnosis, Simmons heads back to the comedy club in an attempt to return to his stand-up roots. It is there he meets Ira Wright (Seth Rogen), a struggling comedian he hires as an assistant/writer. The film then spends a great deal of time introducing us to a group of struggling comedians and actors, and nobody can put together a scene of people hanging out quite like Apatow. He perfectly understands the magic that can happen when you throw an ensemble like this in a room together, but he never lets the joking get in the way of a solid character moment. He may take his sweet time telling a story, but even at their most obnoxious, the characters are so fun to hang out with that the audience is in no hurry to move on.

Unfortunately, with Funny People, audiences finally started checking their watches. It is a long movie, but his first two efforts, The 40-Year-Old Virgin and Knocked Up, weren’t exactly sprints either. With his third film, he just decided to take it to the next level, and audiences were not along for the ride. Perhaps it’s because, for long stretches, the characters in Funny People are self-involved in ways that can very quickly become off-putting. This is especially true of Simmons, who both begins and ends the film as an inherently unpleasant person. That’s certainly the correct choice to make, since any clean redemption arc would have felt phony to say the least, but the film’s dramatic elements prove to be an uneasy mix with the comedy. It helps that the comedy is constantly strong, but Funny People falls victim to simply putting too much on its plate. I still admire the film greatly, even as it struggles to hide the innumerable seams.

As alluded to before, the film hits its roughest patch in the second half, when George and Ira spend some time at the home of Laura (Leslie Mann) and Clarke (Eric Bana). Laura is your typical “one that got away” figure, and in his recovery from cancer treatment George decides to make one last run at her affections. This is when Apatow strays most drastically from his comfort zone, and it just doesn’t work as consistently as all that has come before. When it lives in the world of needy comedians and egomaniacs, there’s a specificity to the universe that proves to be quite alluring. These are clearly people that Apatow understands, and when the film leaves that world behind it feels like a tangible loss. It’s refreshing that the George and Laura plot goes to a rather unconventional end, but the road to that destination is a bit too bumpy for its own good.

You throw all these elements together, and you get a flawed, overreaching, funny and rewarding film. Unfortunately, and perhaps predictably, audiences did not have the patience for it. Despite getting the number one box office spot on its opening weekend (hence me writing about it here), Funny People ultimately bombed, and was unable to earn back its $75 million budget. CinemaScore, which is a lousy way of judging quality but a good way to take a film’s box office temperature, said audiences gave the film a “B-,” which is not good. (If you get anything that doesn’t start with an “A,” that’s normally bad.) Among many people I recall talking to around the film’s release, the word of mouth was mixed at best and toxic at worst. I recall one Facebook status deeming it the worst movie that person had ever seen.

It also says something about the reason most audiences go to the movies, and the way they consume them. As many a CinemaScore result has indicated in the past, the second a film stops being what a typical viewer expects it to be, they often react violently. Typical Adam Sandler fans were likely confused by Funny People, which painted their comedic hero as a sad sack monster and provided laughs in a more subtle way than they might have been used to. On top of that, the film is just a generally odd thing to begin with, eschewing the usual cinematic arcs and rhythms in favor of something more digressive. This is a film that is going to go wherever it likes, whenever at likes, and that concept just didn’t seem to compute with the general public.

This isn’t a new phenomenon to Sandler. Whenever he’s ventured into more dramatic territory, it has usually been met with critical praise and audience indifference. When Grown Ups makes all the money in the world and Funny People does nothing, it’s not illogical for him to go back to what puts bread on the table. It’s frustrating for film fans like myself, of course, but the results don’t lie. This year he took another crack at drama, but both films (Men, Women & Children and The Cobbler) have been met with near-universal derision. You can certainly blame Sandler for making crappy movies 90 percent of the time, and he deserves it, but it’s not as though he completely refuses to try for something bigger. It’s just yet to work out for him.

Funny People can also be blamed for ever so slightly letting the air out of the Apatow bubble. Is that a completely fair assessment? No, but his output has undeniably slowed since then. From 2004-2009, he was involved in comedy hit after comedy hit, but the success hasn’t been quite as constant since then. His next directorial effort, This is 40, was a moderate critical and financial success, and he produced the smash hit Bridesmaids in 2011, but other releases such as Wanderlust and The Five-Year Engagement weren’t quite so lucky. He remains one of the most prominent faces of American comedy, and I’m incredibly excited for his next film, the Amy Schumer vehicle Trainwreck, which is due out in 2015. It suggests that Apatow is taking a break from mining his own brain for inspiration, and Schumer seems like the perfect subject for his sensibilities. As broadly imitated as his improvisational style has become, he may still be the only one that makes it feel wholly natural.