Thirteen years ago, Jonah Hill’s appearance as “eBay Customer” in The 40-Year-Old Virgin didn’t exactly scream “superstar.” In fact, this second feature role didn’t even seem that funny, given Hill’s uninspired facial expression and detached-turned-passive-aggressive demeanor. The joke is that eBay Customer, an awkward male, wants to wear a pair of silver, bedazzled shoes ASAP, which makes the film appear more dated than timely, at least in terms of gender stereotypes. But in retrospect, this brief moment feels indicative of what helped make Hill a comedic star during the subsequent years: eBay Customer seems to be saying “I realize that you don’t fully understand my intent, but what’s important right now is that you pay attention.” As the showbiz saying goes, you have to start somewhere.

Like many, I first became fully aware of Hill’s comedic talent while watching Superbad (2007) for the first time. Sure, I’d recognized his face in the stoner comedy Grandma’s Boy (2006) and certainly, or maybe barely, in Knocked Up (2007). But Superbad is the film that announced him as a new star. In Greg Mottola’s raunchy coming-of-age tale, Hill’s deeply insecure, anti-bro character, Seth, projects a tough exterior — but only with his best pals, Evan (Michael Cera) and Fogell, alias McLovin (Christopher Mintz-Plasse). During the high schoolers’ sexually explicit conversations, Seth’s declarative statements and creative insults are communicated with clarity and eloquence.

Some character actors will forever be associated with specific eras because of their brilliant comedic performances, and for a while, it seemed that Hill would be “That Guy” from 2000s cinema. But something changed.

When Nicholas Stoller released Get Him to the Greek in 2010 — starring Hill as talent scout Aaron Green, who’s tasked to get Russell Brand’s rock star character Aldous Snow to Los Angeles — I initially thought, “here we go again.” But it turns out that Get Him to the Greek’s comedic formula isn’t based on Brand being Brand (clever, edgy) and Hill being Hill (snarky, underappreciated). Instead, there’s a balance between the two, full of pathos, and the film doesn’t entirely rely on their comedic chemistry (see the separate yet hilarious performances by Rose Byrne and Sean “Diddy” Combs).

Thankfully, Get Him to the Greek isn’t steeped in self-deprecating humor based on Hill’s physical appearance. Rather, the film allows Hill to demonstrate his range as a performer, in both vulnerable moments and frustrated character tirades, all the while foreshadowing future roles in which he would complement A-list stars (rather than playing the traditional stooge or straight man). Get Him to the Greek is the primer for bigger and better Jonah Hill productions, and, it must be noted, that a lackluster performance could’ve firmly kept Hill in the 2000’s book of “Where Have They Gone?” cinema. But he succeeded, fortunately, by offering mainstream audiences something new.

Just a year later, Hill’s role in 2011’s Moneyball earned him an Academy Award nomination for Best Supporting Actor. Here, Hill plays the Oakland Athletics talent scout, Peter Brand, who helps Brad Pitt’s Billy Beane buck Major League Baseball’s financial system. Essentially, Hill plays it quiet, complementing Pitt’s subtle fury. Neither performer spirals into an extended rage sequence, nor does either one break down emotionally in a typical “Oscar” moment. Yet, there’s value in these performances (no pun intended), and perhaps it’s the complete departure from typical Oscar-bait performances that makes Moneyball so memorable. In a bad movie, Brand would say something like “I’m very good at my job.” Instead, Hill merely implies the obvious and exudes confidence during the most appropriate moments.

Speaking of confidence, Hill’s character in Martin Scorsese’s 2013 film The Wolf of Wall Street is a complete lunatic. Of course, the same goes for the entire primary cast, as the film satirizes the money-hungry arrogance of Wall Street culture — in this case, during the 1980s. As Donnie Azoff, Hill infuses a sense of mystery to the character. He’s just a little bit stranger than the others because of his wardrobe, bright white teeth, and the mythology surrounding his personal life. That’s good stuff. And by fully capitalizing on this unique character sketch, Hill earned himself another Oscar nomination, one that’s purely memorable amongst a three-hour Scorsese classic full of bizarre, unforgettable sequences.

Most recently, Hill reunited with his Superbad co-star Emma Stone for Cary Joji Fukunaga’s limited series Maniac. Hill once again embraced character mythology by appearing as the various dream-state forms of a single character, Owen Milgrim. While the narrative itself requires patience and certainly isn’t for everybody, Maniac suggests that Hill will continue to keep thinking outside the box.

And given the early rave reviews of his directorial debut, Mid90s (scheduled for an October 19 release via A24), one could argue that Hill is currently laying the groundwork for a multi-decade career with Hollywood mogul potential. And if that’s what’s delaying 23 Jump Street: Medical School, we at Fandor are okay with that.

Q.V. Hough (@QVHough) is Vague Visages’ founding editor and a freelance video essayist/writer. From 2006 to 2012, he lived in Hollywood, California and worked closely with ABC On-Air Promotions as the production manager for LUSSIER. From 2014 to 2017, Q.V. wrote over 600 video scripts for WatchMojo, and he’s the author of their first e-book, WatchMojo’s 100 Decade-Defining Movie Moments of the 1990s. In January 18, Q.V. joined Fandor’s freelance team and currently has four on-going video essay series: Icons + Outliers, Riding the Wave, Between the Lines and Fandor Italian Style. He now resides in Fargo, North Dakota.