1. Funny People (2009)
Judd Apatow’s sprawling mess of a movie is the most fascinating cinematic mixed bag since A.I. brought us ultraviolent murder carnivals and cutesy CG characters voiced by Robin Williams within an hour of each other. There’s a lot to love and hate, but what’s not really debatable is how painfully unfunny the standup is, whether it’s coming from the allegedly brilliant but compromised celebrity played by Adam Sandler or the allegedly promising young star played by Seth Rogen. Sandler and Rogen are very funny people, and they’re performing a script written by a guy who’s had a hand in almost every funny thing that’s happened in movies for the past decade. So why is James Taylor funnier onstage here than either one of them? Seeing otherwise hilarious people spouting the unfunniest material of their careers when we’re supposed to believe they’re geniuses would be Funny People’s fatal flaw if it didn’t already have so many other problems (an insane running time, dozens of distracting cameos, the presence of Paul Reiser). - Scott Howard

2. Studio 60 on the Sunset Strip (2006-2007)
At least comedians like Funny People, which could not be said of Aaron Sorkin’s notorious return to the tube after being backdoor fired from The West Wing following a string of PR disasters, including an arrest at the Burbank airport when his crack pipe set off the metal detector. Even fellow NBC employees Tina Fey and Conan O’Brien publicly mocked its pompous portrayal of comedy writers as the last bulwark of intellectualism against the slack-jawed neanderthals in flyover country. Comedy as the lone voice of sanity for the politically isolated isn’t all that odd of an idea for those of us who found solace in the arms of The Daily Show and The Colbert Report in the Dubya era, but those shows crank out brilliance every night. Studio 60‘s supposed wunderkind Matthew Perry prefers Gilbert & Sullivan parodies, and his signature piece is a sketch called “Crazy Christians” that is so explosive it threatens to sink the entire network. What’s it about? CHRISTIANS who are CRAZY! The much stronger dramatic material involving network execs Steven Weber and Amanda Peet proves that Sorkin should quit trying in vain to make us laugh. - SH

3. Coyote Ugly (2000)
One song is all it takes for Piper Perabo’s plucky heroine in this 2000 snore to ascend from part-time bar-dancer to hit songwriter with a record deal, and while not as torturous as the song Roger struggles to write to save his soul in RENT, it’s just as forgettable. But “Can’t Fight The Moonlight” isn’t just bad: It’s the bad that can now be heard in every pharmacy line and dentist’s office in the world because of the song’s post-movie chart climb. If only LeAnn Rimes’ latest tabloid exploits would force Clear Channel to push for a ban on this syrupy pap. - Ellen Wernecke

4. Sex and the City (1998-2004)
Carrie Bradshaw is the worst columnist that ever existed ever. She’s worse than a hack — she literally can’t form a coherent essay. Her column reads like the most vapid, self-absorbed blog ever written, except that we’re supposed to believe that not only does she write for the New York Observer and Vogue, but that she actually gets a book deal. Her columns are filled with never-answered questions. “Why is it that we always seem to want what we can’t have?” Carrie might muse, typing furiously on her MacBook as if this was a Huge Revelation For Everyone. One can only attribute her column’s success to the idea that there was a large and devoted gathering of New Yorkers who read it solely to mock her. Or else, like the show itself, we’re supposed to think it’s good simply because it’s marginally relatable. See, her life is like ours! She asks the questions we ask! God, is this amazing or what? I do take some joy, though, that with the rise of good blogs and the death of the newspaper, Carrie’s job would be the first to be axed. - Zoe Holmes

5. Reality Bites (1994)
This instantly dated ’90s dramedy is forgiven for making Ben Stiller the bad guy and Ethan Hawke the hero, because in 10 years no one will understand why we were all rooting for Michael Cera. But Stiller’s supposed crime hasn’t just lost its odious reek because the commercialized Aughties make selling out okay: It’s because the Winona Ryder character’s documentary, from what viewers see of it in the making, is bound for the Self-Righteous section of the video store. The shabby rebellion captured through her lens wouldn’t even make the cut for MTV’s True Life. Turning it into a wacky ad may have been the best thing that ever happened to her. - EW

6. The Phantom of the Opera (1986)
The masked man at the center of Andrew Lloyd Webber’s perennial hit musical is described by the mysterious ballet mistress Madame Giry as “a genius, an inventor, an architect, a magician, a composer.” During the course of the show, he reveals a number of other skills: vocal coach, fashion designer, interior decorator, murderer. Given this impressive resume (and the fact that he’s been sulking around in an opera house for the vast majority of his life), you’d think he’d have something dynamite in store for his debut opera. Alas, after he appears amidst a blinding pyrotechnics display to demand the performance of his magnum opus Don Juan Triumphant, our excitement quickly subsides when it’s revealed to be an atonal mess designed solely to torture the audience. Webber would probably defend Don Juan as a dark peak into the mind of a madman, but it’s hard to believe the guy who belted “Music of the Night” an hour earlier couldn’t come up with something better than this. - SH

7. Hamlet 2 (2008)
Steve Coogan’s attempted stateside breakthrough about an “inspirational’ high school drama teacher is supposed to be a comedy, but the film’s penultimate musical number was the least funny seven minutes shown in film that year. Coogan’s hapless Dana Marschz beams with pride as his students perform the opener to their musical-within-a-movie, the piquantly titled “Raped In The Face,” and the onscreen audience registers shock — while the offscreen audience checks its watch and wonders whether it will ever laugh again in this life. It’s almost enough to ruin the sheer brilliance of those same high schoolers shimmying to “Rock Me Sexy Jesus” just a few minutes later. - EW

8. Prêt-à-Porter (1994)
Released on the heels of his victorious comeback films The Player and Short Cuts, Robert Altman’s Prêt-à-Porter (released in the U.S. as Ready To Wear since Americans presumably don’t like to speak French) was highly anticipated before its release but is now largely considered a trifle, one of Altman’s loose experiements that never really gels. There’s a bit of fun in the people-watching; it’s unlikely you’ll ever see Björk, David Copperfield and Cher in the same place again. The much-discussed finale, however, is ridiculous. In it, a designer sends out an entire runway of nude models. The fashion press heralds it as a brave and brilliant celebration of the human form. Altman is commenting on the vacuousness and groupthink of the fashion world, but in lazily retelling the Emperor’s New Clothes for the ten-thousandth time, he’s not making any grand new statements either. - SH