[3] His parents are Sharon Lyn (née Chalkin), a costume designer and fashion stylist, and Richard Feldstein, a tour accountant for Guns N' Roses.

Their older brother, Jordan Feldstein (1977–2017), was a music manager for Robin Thicke and Maroon 5 until his sudden death at age 40 from a pulmonary embolism.

[25][26][27][28] In college, Hill began writing his own plays and performing them in the Black and White bar in the East Village neighborhood of New York City.

On television he played the "RA Guy" on the first season of the Oxygen Network sitcom Campus Ladies, and guest-starred in an episode of Clark and Michael.

[36] Hill wanted to be a writer since he was young and dreamed of joining the writing teams of The Simpsons, Saturday Night Live, and The Larry Sanders Show.

[38] He guest starred in The Simpsons episode "Pranks and Greens", portraying an immature man named Andy Hamilton who was hailed the best prankster in Springfield Elementary School history.

[41][42][43] In July 2011, he appeared at ESPN's ESPY Awards sporting a much slimmer physique, stating he had lost 40 pounds (18 kg).

In November 2011, along with Sam Worthington and Dwight Howard, he starred in commercials for the video game Call of Duty: Modern Warfare 3, making his first appearance with his new look.

[47] In 2011, Hill starred in Bennett Miller's feature film Moneyball with Brad Pitt and Philip Seymour Hoffman.

[54] Citing a possible conflict with his commitment to The Watch, Hill lamented that to act in a Tarantino movie was "the perfect next step" in his career.

[56] In 2013, Hill appeared in This Is the End as himself, and in the biographical film The Wolf of Wall Street,[57][58] and received his second Academy Award nomination for his work on the latter.

In an interview with Howard Stern on January 21, 2014, Hill said he had accepted SAG's minimum wage of US$60,000 for Wolf of Wall Street.

[59] He voiced the Green Lantern in the adventure comedy The Lego Movie in February 2014, which blends computer animation and live action.

[69] Hill made his directorial debut from a screenplay he wrote with the film Mid90s (2018) starring Sunny Suljic, Lucas Hedges, and Katherine Waterston.

[71] Also in 2018, Hill starred as Owen Milgrim in the Netflix dark comedy miniseries Maniac alongside Emma Stone.

[74][75] In 2020, Hill appeared alongside director Martin Scorsese in a commercial for Coca-Cola Energy, titled Show Up which aired during Super Bowl LIV.

[76] Hill was cast in Adam McKay's political comedy satire Don't Look Up alongside Meryl Streep, Leonardo DiCaprio, Cate Blanchett, Jennifer Lawrence, Timothée Chalamet and Mark Rylance.

[79] In November 2021, Hill was cast as Jerry Garcia in the biopic feature of the Grateful Dead directed by Martin Scorsese.

[84] In July 2011, Hill appeared at the 2011 ESPN ESPY Awards having lost a significant amount of weight; he later said he had done so to seek more serious roles.

[85] In 2016, Architectural Digest reported that Hill bought a four-bedroom loft in the Noho neighborhood of Manhattan in New York City.

[88] Hill says: "TM [transcendental meditation] along with surfing, I'd say that those two things have changed my happiness level and my ability to cope with stress, anxiety and depression… [they've] really helped.

[94][95][96] During the same month, former child actress Alexa Nikolas accused Hill of shoving her against a door and kissing her without her consent during a party at Justin Long's house when she was 16 years old and he was 24.