When Todd Phillips talks to aspiring filmmakers today, his advice goes something like this: “You just have to go out and do it and believe in an idea whether it’s a documentary, or a script that you wrote. You’ve got to be totally passionate about it… The intention shouldn’t be to make a calling card. You need to truly believe in the project that you are doing.”

He knows what he’s talking about. You have to want to make a movie pretty badly to drop out of film school to complete it and then have your star break parole (and eventually get re-arrested) to participate. It’s a long and somewhat apocryphal story, but suffice to say Phillips, then an ex-junior at NYU, really wanted to make his feature-length documentary Hated: GG Allin and the Murder Junkies, which became the highest-grossing student film of its time, and even secured limited theatrical release. Side note: In a case of life imitating documentary life, if such a phenomenon exists, the NYU premiere imploded due to the antics of the subject it chronicled.

Though the connection between transgressive punk rocker GG Allin and ultra-chill folk rockers Phish may not be readily apparent to the naked ear, the jam band contacted young Phillips—who was not initially a phan—to chronicle their 1997 tour in the doc Bittersweet Motel. Maybe they recognized Phillips’ keen eye for story and an instinct for letting his subjects do the telling, even in his thus far limited body of work.

If those films aren’t sounding familiar yet, stay with us. While at Sundance for his Grand Jury Prize-winning doc Frat House, he met producer and director Ivan Reitman who sensed a certain humor in Phillips’ documentary work and encouraged him to try his hand at comedy features. You don’t get to be Ivan Reitman without a sixth sense for talent, and Phillips subsequently created—as a producer, writer or director, and sometimes all three simultaneously—Road Trip, Old School, Due Date and oh yeah, The Hangover trilogy. For good measure, he acted in a number of them as well (watch for an oddly consistent series of appearances by a guy in a track suit and a black curly wig). If those comedies, along with School for Scoundrels and Borat, established an affinity for a certain kind of movie (Details magazine dubbed Phillips, Judd Apatow, and Adam McKay “The Frat Pack” in 2005), The Hangover trilogy’s box-office smashing $1.4 billion gross probably cemented it. Whether they’re your kind of movies or not, they’re testament to Phillips’ canny knack for bringing together the right combination of really funny people and sitting back to watch the pandemonium. It hasn’t hurt the careers of guys like Will Ferrell, Zach Galifianakis or Ed Helms, either.

But cloaked in the gags, over-the-top antics and buffoonery is a certain vulnerability that derives from male characters carefully navigating relationships with other men and struggling into often-delayed adulthood with their egos intact. You get the feeling that it’s in these moments Phillips’ work comes from its most honest place.

Phillips recently told the Los Angeles Times “The nature of movies with great characters is to make us ask, ‘Why am I rooting for them?’ I was rooting for Al Pacino in Scarface even though he’s the worst guy in the world.” So we’re expecting to root for the protagonists of his new film War Dogs. It’s not about frat houses, and this time, the road trip is no joke. In some ways it’s a departure for Phillips, but not entirely, because a movie about two brash and misguided guys in over their heads is funny, even when it’s not.