Todd Phillips is one of the most fascinating filmmakers working today, especially when considering his future and the potential he has after completely shifting his style midway through his career. When he first began directing movies, Phillips made teen comedies no different from the likes of American Pie, but the late 2010s saw a radically different Phillips behind the camera.
How he was perceived by audiences and critics has changed drastically since the early 2000s, as has his box office results. After several modest successes, the director found himself breaking one box office record after another. Phillips currently holds the record for directing the highest-grossing comedy of all time and the highest-grossing R-rated movie of all time.
School For Scoundrels (2006) - $24.4 Million
School for Scoundrels is a remake of the 1960 movie of the same name, but while the original British movie is charming, pleasant, and hilarious, the same can't be said for the 2006 version. Phillips' movie can barely even be called a remake, as the plot is entirely different from the original, and it has a distinctly cruel tone too, which was criticized at the time.
The movie is about a man with low self-esteem who signs up to a class that promises to build his confidence, only to be relentlessly bullied by the teacher. Because of this, the movie was a box office bomb, failing to even recoup its budget of $35 million. While the 1960 movie isn't exactly an IP that has millions of fans, if the remake was more faithful to the original, it could easily have been way more successful at the box office.
War Dogs (2016) - $86.2 Million
Following the approach that War Dogs is a well-crafted satire. The film is based on a true story and it follows a massage therapist who falls backward into global arms dealing, and then somehow gets contracted by the U.S. Army to supply $300 million worth of ammunition to the Afghan National Army.
While the movie is hugely entertaining and has major star power behind it, as Miles Teller and Jonah Hill play the lead roles, it still underperformed at the worldwide box office. But regardless of its disappointing box office results, it finally saw Phillips' being critical of his protagonists' behavior and making them pay for their actions.
Old School (2003) - $87.1 Million
Coming from early 2000s Phillips, the plot of Old School is as typical as it could possibly get. The 2003 comedy is a college movie, but instead of following students in their late teens and early 20s, it follows sad middle-aged men trying to recreate the best time of their lives by starting a fraternity.
With a budget of $25 million, Old School did just fine at the box office. However, almost 20 years later, it doesn't get talked about as much as it should when debating great 2000s comedies. The film might have been a modest success, but it's still one of the several overlooked Will Ferrell-led movies that don't get the recognition they deserve.
Road Trip (2000) - $119.7 Million
While there are plenty of underrated road trip movies, the 2000 movie is one of the most thoroughly entertaining. Road Trip follows a group of misfits attempting to retrieve a sex tape that was accidentally mailed to one of their girlfriends. One of the biggest movie trends of the 1990s and 2000s was the teen comedy, and Road Trip is one of the tentpoles in the genre, though it wasn't necessarily expected to be.
Road Trip was Phillips' directorial debut, and a $119.7 million box office intake is a success that most first-time directors can only dream of. But it was clearly helped by several recognizable faces such as Seann William Scott, Tom Green, and Breckin Meyer, and it was obviously trying to appeal to a specific audience and demographic.
Starsky & Hutch (2004) - $170.2 Million
Even though it isn't saying much and he isn't exactly the most seasoned actor ever, Snoop Dogg's best movies. The movie is again a remake of a much older property, the procedural '70s crime show of the same name, only it's a lot more faithful to the source material than School for Scoundrels.
Interestingly, the film did what Saturday Night Live alumni, which helped it gross a very respectable $170 million.
Due Date (2010) - $211.7 Million
Just like how Due Date and Planes, Trains, and Automobiles, as they both follow an everyman who is lumped with an unstable and emotional loser. And like Phillips' directorial debut, Due Date is a road trip movie too.
The movie, unfortunately, lives in the shadow of the Hangover series, as it's sandwiched between the first two movies in the hit comedy franchise. However, while it wasn't the phenomenal hit that The Hangover was, it was a success upon its release, making three times its budget.
The Hangover Part III (2013) - $360 Million
The Hangover Part III seemed like Phillips was bored of the franchise, as the movie doesn't even feature the series' signature hangover (albeit except for in the post-credits scene), and is more of a crime caper. And that's almost the exact reason for relatively abysmal box office intake. While $360 million is usually a huge success for a comedy movie, it could also be looked at as a massive disappointment in other ways, and that's exactly what it was deemed by the studio.
Not only did Part III make more than $200 million less than the second movie, but it even made $100 million less than the original too, which is not exactly what's expected of the third film in a smash hit series. On top of that, the movie had an inflated budget of $103 million, which is an absurd amount for a comedy movie, and it meant that the gross profit was even less.
The Hangover (2009) - $469.3 Million
With a budget of $80 million, the studio had a lot of faith in The Hangover during development, as a film like this could have had a significantly lower production cost. That figure especially sounds like a lot considering that the only movie star in the film was Bradley Cooper, who wasn't even that bankable at the time.
And though Jack Black almost played Alan, general audiences had no idea who Zack Galifianakis was. But the studio was right to invest so much into it, as it massively overperformed at the box office and Phillips repeated the success he had with Road Trip, only on a much bigger scale.
The Hangover Part II (2011) - $586.7 Million
Interestingly, where sequels usually have much bigger budgets than their predecessors, The Hangover Part II had the same budget as the original. It's hardly surprising, as Part II has the same formula and story beats as the first movie, only it's set in Bangkok instead of Las Vegas.
While the 2011 sequel could never top the original Hangover in comedy and excitement, in of box office success, it blew the original out of the water. Setting aside animated movies and films with high concepts, The Hangover Part II is the highest-grossing comedy of all time.
Joker (2019) - $1.074 Billion
Before it was widely released in 2019, nobody thought the director of The Hangover could have made a gritty and compelling movie about one of the most sadistic and iconic villains of all time. But Phillips proved everybody wrong and surprised audiences by directing a truly original and fascinating take on the Clown Prince of Crime.
Joker has become the highest-grossing R-rated movie ever, which could surely only be outdone by its potential sequel. What makes the box office more impressive is that the movie was shot on a shoestring budget of $55 million. That means that considering marketing costs and movie theatre cuts, Joker must have earned a gross profit of $900 million.
