He replaced Kyle Riabko as Melchior Gabor in the First National Tour of Spring Awakening, officially beginning his run on July 7, 2009. Epstein commented on the show, "I think it really doesn't talk down to its audience. I think it portrays teen sexuality in a way that's real, in a way that's entertaining, and in a way that's just really connects with people. Spring Awakening really doesn't hold back, and I think people appreciate that." Also in 2009, Epstein starred as CB (a.k.a. Charlie Brown) in Dog Sees God: Confessions of a Teenage Blockhead, described as a "comedic deconstruction of the famous Peanuts characters." In this production, CB copes with the recent death of his beagle and discovers that he is in love with Beethoven (a.k.a. Schroeder). Theatre critic Richard Ouzounian wrote, "Jake Epstein is brilliant as CB, a bunch of nerve endings searching for a place to settle. Epstein is so beautifully open and honest that you go with him on every step of his journey." In July 2011, Epstein played Billy's older brother in a Toronto production of Billy Elliot the Musical. He spoke about working with alternate leads, "The most unique part of this show is working with a new Billy every night. Every Billy is different. They each bring something interesting and specific to the role. I am a different older brother each night, depending on who's on..." He played Will in Green Day's Tony-winning rock musical American Idiot during the 2011–2012 North American tour. Epstein said, "I always think of American Idiot as my generation's The Who's Tommy or Pink Floyd's The Wall. American Idiot was very much like that time in the world, right after Sept. 11th...It was like a time of not knowing what to feel and that's what spawned this show." In a 2013 interview, Epstein identified Will as the most challenging role he had ever played. He said, "I sat on a couch and never left the stage for the majority of the show. That experience was a whole lesson in pacing, in creating a whole world for yourself on stage, and in letting the experience you are having that night dictate your arc for the show." Epstein made his Broadway debut in Spider-Man: Turn Off the Dark as the alternate for lead role Peter Parker/Spider-Man. He joined the company on December 4, 2012, and performed Saturday and Sunday matinees,