8. War Dogs (2016)
Jonah Hill was cast as one of the leading stars in a movie from the director known for The Hangover and immediately expectations were cast in the wrong direction. What might have seemed like a comedy, and what was certainly promoted as a comedy with a touch of the darkness present in the likes of Andrew Niccol’s Lord of War, was actually a politically indecisive commentary on worldwide arms deals with little by the way of fun and even less by the way of important things to say.
The shell of War Dogs was undeniably promising, and Phillips’ history in documentary filmmaking complimented the mood of the time (and the political films being released – Spotlight, The Big Short, etc.), but of all of the “comedy director makes something serious in an off-beat way” films of the era, War Dogs is the most forgettable for a reason.
Miles Teller, who had excelled at the lead of Whiplash and had already made a name for himself as a go-to actor of immense talent in independent filmmaking, seemed stifled and uninvested, which contrasted the performance of his co-star Jonah Hill who was quickly establishing his name as an actor with talents far surpassing those of being a simple comedy sidekick. The resulting screen partnership was as confused as the wider film, Phillips and company never quite hitting Lord of War levels of dark humour, satire and relevance, and War Dogs becoming the best of the worst films of Phillips’ career as a result.
7. Road Trip (2000)
Under the watchful eye of Ivan Reitman and burgeoning mega-studio Dreamworks, Todd Phillips captured the mood of the time in his 2000 college road trip movie Road Trip.
Nu-Metal was hitting the Hot 100, baggy jeans and unnecessary goatees were all the rage, and American cinema was convinced that all male teens and young adults were sex-hungry, repulsive human beings with hearts of gold, whilst all women were either the unquestioning images of perfection all men wished for, or cheaters with something to hide.
In Road Trip, Todd Phillips and company not only embraced these trends to hit a major young-adult market, but importantly they evolved these archetypes beyond those seen in American Pie and the like, evolving the genre away from its problematic roots in the process. Road Trip isn’t the bastion of good taste by any means, but characters were given more to do than just be creepy or hot, and this evolution made each of the characters in Road Trip all the more relatable.
As a time capsule, Road Trip remains fascinating, and for anyone inclined to enjoy a romance-centred comedy about a group of guys being guys, there are memorable moments and it is certainly a lot of fun. If the first few entries in this list were indicators of the bad movies Todd Phillips has made, this entry begins our foray into the good movies released under his name.
Todd Phillips Cameo: Plays the creepy guy on the bus who tries to lick Beth’s (Amy Smart’s) toes while she’s asleep.
6. The Hangover Part II (2011)
After the huge success of The Hangover two years prior, Warner Bros sanctioned a sequel almost immediately, and sniffing the opportunity to solidify his name amongst the best of comedy filmmakers in his era, Todd Phillips doubled-down on his ‘better than soundstage comedies’ approach for The Hangover Part II.
Part II may not have been set in Las Vegas, but its narrative played out even more like a heist film than the original. Borrowing almost exactly the same narrative as was used in the first film, right down to specific beats, but evolving them in the typical sequel fashion – bigger, brighter, more exotic – The Hangover Part II felt more Inspired by the works of Steven Soderbergh on his Ocean’s Trilogy, and more confident in some filmmaking respects, not least in terms of pacing (which is some of the best on offer in all of Todd Phillips’ filmography).
A standout feature of The Hangover Part II are Phillips’ references to not only his first Hangover film, but to the films of his earlier career, a neat call-back to the memorable river jump in Road Trip (which was evolved for Starsky & Hutch) being the most obvious.
The Hangover Part II places where it does in this list because it was a project that demanded more of the same from a director who until this point had made attempts to be original, and despite this film effectively showing off some of Phillips’ most prominent filmmaking talents, simply didn’t shine as brightly as the films to come in terms of standout filmmaking attributes and importance to Phillips’ filmography (and cinema as a whole).
Recommended for you: Ocean’s Movies Ranked