‘The 40-Year-Old Virgin’ (2005)
We’re not sure what was funniest about Hill’s one scene: his deadpan delivery, the garish disco boots, or the concept of a brick-and-mortar eBay store.
‘Knocked Up’ (2007)
Having been inducted into the Judd Apatow family in 2005’s “The 40-Year-Old Virgin”, Hill was granted a slightly larger role (i.e., his character got a name: Jonah) in this movie that came out a month before “Superbad”. After that came out, Hill’s days of playing characters so inconsequential they’re named “Jonah” were behind him.
The watershed moment in Hill’s career in which he pretty much played a young Seth Rogen to Michael Cera’s young Evan Goldberg (i.e., the film’s writers) in this warts-and-penis-drawings-and-all depiction of some lovable losers’ last night of high school. Another film where the chemistry of the two male leads was integral to its success, ‘Superbad’ was a sign of what was to come for Hill, whose most successful roles to come had him share the marquee with other guys.
‘Get Him To The Greek’ (2010)
Armed only with a bit part in 2008’s “Forgetting Sarah Marshall”, Hill, with his performance, convinced its creative team of Jason Segel and Nich Stoller that his chemistry with Russell Brand deserved its own feature film. Brand plays the same out-of-control rock star (if it ain’t broke, right?) with Hill going from waiter to intern, tasked with – you guessed it! – getting him to the Greek. Like many Judd Apatow productions, this one had a lot of vomit and a lot of heart.
Something of a first for Hill, ‘Moneyball’ proved there was more to this guy than gross-out comedy. The rotund actor held his own opposite Brad Pitt in this true tale of baseball economics, playing the upstart who introduces the concept of ‘moneyball’ to the Oakland Athletics. The movie led to other roles in which he rubs shoulders with good-looking men. Not coincidentally it was also around this time that Hill hit the gym and dropped an astounding amount of weight. Oh, and did we mention the Oscar nom?
‘Allen Gregory’ (2011)
At the height of his powers, Hill turned to animated television for this pet project he co-created, wrote, and starred in. Hill voiced the titular character, a precocious and urbane seven-year-old who must adapt to a new life at a typical elementary school. The reviews were not kind to the show, representing Hill’s first major misstep in his career. Personally, I really liked the show but I am clearly in the minority.
’21 Jump Street’ (2012)
Those who thought he had excellent on-screen chemistry with Michael Cera hadn’t seen anything yet. This smart remake of the ‘80s show (not often you can say that!) literally partnered Hill with Channing Tatum as the cops who go undercover at a local high school to say no to drugs. Hill contributed to the story and was instrumental in getting Tatum on board, so sure was he that the hunk had many funny bones in his buff bod.
‘This Is The End’ (2013)
The whole gang – plus several notable cameos – reunite for this self-reflexive look at life after the end of the world. Seth Rogen and Evan Goldberg penned this dark comedy that cast their friends as themselves for a clever genre film. Jonah Hill is in there somewhere.
‘Hail, Caesar!’ (2016)
Hill continued working with some of the best directors in the biz on “Hail, Caesar!”, the 2016 comedy from the Coen brothers. Contributing to a stellar ensemble cast, Hill was reunited with “Jump Street” co-star Channing Tatum but played alongside Scarlett Johansson in this look at the waning Hollywood studio system of the 1950s.
‘War Dogs’ (2016)
Miles Teller and Hill play arms dealers who are hired by the US Army to supply weapons to the Afghan Army in this “very loosely based” true story. Though the critics were split on the film as a whole, the Hollywood Foreign Press at least thought Hill’s performance deserved to be singled out, granting him a Golden Globe nom for Best Actor in a Comedy/Musical.