Growing up in Fairfield, Connecticut, Wolf's older brother, Rich, played bass in a high school band called Villanova Junction which featured future hometown hero John Mayer. Inspired by watching the band rehearse, Jim later taught himself to play guitar and sing and in the mid-2000s launched his own music career. Singing in a smooth, warm voice reminiscent of Mayer's, Wolf forged his own melodic folk-pop sound on early releases like 2005's No Sleep What-So-Ever and 2007's Stars Never Lie. He then moved to New York to better his chances at success, releasing 2010's Sleeping with Strangers and the 2012 EP Strange, Weird, and Romantic, Pt. 1.
At this point in his career, Wolf had achieved only moderate independent success in the U.S., but in 2014, two popular South Korean actors, ChaeRim and Gao Zi Qi, featured a song from his previous EP in their highly publicized wedding. "Make You My Lady" went on to become a hit song on the South Korean charts, at one point in late 2014 peaking even higher than Idina Menzel's "Let It Go." Even more unexpected than its initial fame was the song's continued success, much of it thanks to its use in various television shows, most of them popular K-dramas. With "Make You My Lady" still in the charts, Wolf embraced his new Asian pop audience and continued to release new music during the latter half of the decade including a second volume in the Strange, Weird, and Romantic series and 2020's Forever Sunday album. In 2021 the single "I'm Here for You," along with several other songs was featured in another popular show. Wolf celebrated his continued success with the release of the full-length Strange, Weird, and Romantic, Pt. 3. ~ Timothy Monger, Rovi