Every Todd Phillips Movie Ranked Worst To Best

Now for the curious case of Todd Phillips. After directing some of the funniest comedies of the 21st century with "Old School" and "The Hangover" trilogy, his career looked a lot like his fellow "frat pack" friends Judd Apatow ("The 40-Year Old Virgin) and Adam Mckay ("Anchorman"). That was before his pivot to making one of the best dramas of the millennium with "Joker" in 2019. Maybe the old Hollywood maxim that comedy is the toughest genre is true. If you can make people laugh, making them cry is easy. 

The Bronx-born Phillips was a film school dropout but pursued the life of a documentarian. In the '90s he appeared as one of those prodding producer-drivers on HBO's "Taxi Cab Confessional," but his real work was on a series of underground docs about male depravity. However, Phillips made his bones in Hollywood as a screenwriter. Ivan Reitman of "Ghostbusters" fame discovered Phillips and gave him this big break. Phillips had his hands on "Borat" and then punched his own ticket with the scripts for "Road Trip" and "Old School." Billions in box office revenue followed. Phillips has been on fire for decades, but when he made his pivot to more serious cinema, it was ironically a movie about a failed comic. What on Earth would Todd Phillips know about failure? Not much, but we're still going to rank his movies from worst to best. 

Following "The Hangover," audiences wanted more of the eccentricity of Zach Galifianakis. Released in 2010, "Due Date" is sort of Warner Brothers' effort to unofficially remake "Trains, Plains, and Automobiles," with Galifianakis in the John Candy role and Robert Downey Jr. as the exasperated Steve Martin-style character, Peter Highman. Peter is about to have his first child but misses his flight because of interference from part-time actor and full-time idiot ​​Ethan Tremblay (Galifianakis). From there it's a road movie, and hijinks ensue.

Galifianakis and Downey's star power carried this film to a tidy profit in theaters, but it doesn't work. Neither critics nor audiences liked it. Downey is great as always as an exasperated straight man, but coming off "Iron Man," he's best in the wise-cracking driver's seat. Yet, Galifianakis as Tremblay is such a revolting doofus that he will wear on your nerves.

Danny McBride makes a great cameo as an impatient Western Union employee eager to get to his dinner reservation at Chili's. McBride was like a skeleton key for comedies in this era. Comedy directors could just plug him into their movie in any role — no matter how minor — and he'd steal a scene or two.

Documentary filmmakers and jam bands have something big in common: Both approach their craft with an established set of tools, but there is no script. Each finds the story along the way.

Released in 1997, "Bittersweet Motel" about the notable jam band Phish is the second music documentary of Todd Phillips' early career. Phish is maybe the second biggest name in chilled-out and loosely organized psychedelic song-craft after The Grateful Dead (Phish fans sometimes loathe the comparison).

"They don't know what's going to happen, just like we don't know what's going to happen," remarks bassist Mike Gordon, referring to his fans showing up for the band's ever-changing setlist. This isn't a group that ever had radio hits. They built their cult following on tour from the ground up. And it is a literal following, as their fans travel with the band. Phillips himself followed the band for two years, capturing backstage stuff and the humble musings of the group's reluctant leader and virtuoso guitarist, Trey Anastasio. This doc mostly has the underground feel of Phillips' first two films, and given the trail mix and sandals mentality of these genial rockers, it works.

"You hear that Mr. Anderson? That is the sound of inevitability." That scene of Agent Smith (Hugo Weaving) talking to Neo (Keanu Reeves) in "The Matrix" is probably a little what Warner Brothers sounded like pressing Todd Phillips and company to turn "The Hangover" into a trilogy after the record-shattering returns of the first two films.

Phillips' approach to pulling this off again was to lock himself in a room with screenwriter Craig Mazin as the two just tried to make each other laugh. He also relied on feedback from star Zach Galifianakis. "There's nothing better than when Zach texts me and says, 'I read that scene. Dying,'" Phillips told Vanity Fair. And this film does put the focus on Galifianakis' man-child, Alan. He's off his meds and more obnoxious than ever, but when The Wolfpack does an intervention and tries to get him to an in-patient clinic, another wacky road trip ensues.

Some in the press were hard on the second installment. After all, how could the same thing happen to these guys twice? Comedy follows a rule of threes, so Phillips' response was to triple down. "We were like, 'Oh yeah? It's going to happen three times.'" Critics responded in kind, and "The Hangover Part III" has the worst Rotten Tomatoes score of Phillips' career. Maybe this series didn't finish strong, but it still made a bucket of money — over $362 million globally.

Todd Phillips grew up in a house with his mother and two older sisters, and there were no fraternities at New York University, where he briefly went to film school. Despite the assumptions about him, he says he's not like any of his bawdy characters. As he said at SXSW, he was "never really exposed to a lot of male relationships," but always found them awkward and fascinating.

That definitely translates to the 2004 buddy cop comedy "Starsky & Hutch." Phillips also says he's drawn to comedies that feel "grounded" in the real world as is the case with "Stripes" (one of the director's favorites) rather than the more out-there antics of films like "Austin Powers." "Starsky & Hutch" is goofy, but it's also a police procedural that walks the line between these two modes. Owen Wilson and Ben Stiller play the titular cops who want to take down a menacing drug kingpin, played with tremendous verve by Vince Vaughn at his tempestuous best.

The critical reception wasn't exactly ecstatic, but the $170 million box office was decent. Once again, Phillips was in the comedic catbird seat. Stiller's uptight Starsky contrasts nicely with Wilson's laid-back Hutch, and this movie stands as a time capsule of two of the funniest and most charming Hollywood performers ever doing exactly what they do best. 

"War Dogs," a funny but often deadly serious film about two reckless war profiteers marks Todd Phillips' transition away from fratty comedies. Adapted from a true story first published in Rolling Stone, the director had a new challenge. "This is definitely a trickier tone than what I've done before because of that balance with the comedy and the drama," he told The Off Camera Show.

Both aspects work thanks to phenomenal turns from Jonah Hill and Miles Teller as two childhood friends who find a clever and amoral way to get rich quickly. They act as a third party, selling arms in various global hot spots where the US government won't deal directly. They love the high life, but when they land a $300 million contract to supply weapons to Afghan troops, they begin to crack under the pressure.

Like "The Wolf Of Wall Street," "War Dogs" is a rise and fall story about two young men undone by greed, but really, these merchants of mayhem are part of a much bigger game. "There is an underbelly to [the United States military] where a lot of people make a lot of money," Phillips told The Movie Times, "and these are two guys that try to get in on that."

Coming off the down note of his first bomb, "School For Scoundrels," in 2005, Todd Phillips bounced back with the highest-grossing R-rated comedy of all time. "The Hangover" made nearly half a billion dollars globally and turned the once obscure piano-playing, alt-scene-comic Zach Galifianakis into a household name. And it's hilarious for 100 straight minutes — all while being shot with the slickness of a big-budget action movie. 

You know the story: Four guys go to Las Vegas for a bachelor party but get so wasted they lose the groom and spend the entire next day piecing together what happened. Phillips didn't write the script, but he was the right man to direct the boys-will-be-boys debauchery.

Mike Tyson, of course, makes a great cameo as a kind of Nevada kingpin version of himself. The Wolfpack, as these guys call themselves, has a run-in with the former champ and his tigers during their wild night. Phillips recalls how funny the former fighter was on set. During the scene in which Tyson knocks out Galifianakis' character, he kept pulling the punch, and it didn't look right on camera. Finally, Phillips had to come over and show the boxer how it's done. Phillips recalled Tyson's reaction to the irony to James Corden, "Oh, this is great," Tyson joked, "I'm getting boxing lessons from the captain of the Jewish debate team."