In 2019, Jack Rutstein released breakout single Two Face off of his first mixtape Long Story Short. The mixtape also featured a frequent collaborator of Rutstein's, The Young Xp who allowed Rutstein to remix his song Mordecai and the Rigbys (Remix). Rutstein's 2020 debut album entitled 2lips grew to amount to over 75,000 streams on Spotify, landing him on Chicago label Minty Fresh Music with a talented set of self-written solo records. Since, Rutstein has found himself performing at venues like the Loud N Proud festival and Nickel Plate amphitheater, where he opened with Christian French after their collaboration on heavy snow. After four singles that demonstrated Rutstein's versatile harmonies with EDM track Lonely Road or bedroom pop April Showers, Rutstein stepped aside briefly to focus on songwriting demos for other artists. Rutstein recently was the songwriter behind Johnny Orlando's blur and get me high by Marco Luka. Rutstein's hit record has been teased as a visual "American Honey," paying reverence to the 2016 Andrea Arnold film. In 2023, Rutstein released "After We Move On" with features from Anne-Marie, 97BROKEN, Connville, & The Young Xp. Rutstein shares that he feels "relieved anytime I'm releasing music, it's personally vulnerable and a creative way to express myself" It's fair to say there's a Rollercoaster of feelings in Rutstein's love life, with each record seemingly covering someone new, either in love or heartbreak. In 2024, Rutstein released J'abandonne!.