In early 2014 as IshDARR was preparing to release his debut solo EP, he was contacted by an
A&R representative at
Epic Records, Amanda Berkowitz. She would later become IshDARR's mentor and co-manager. In March 2015, he released his first mixtape,
Old Soul, Young Spirit, which featured the single "Too Bad". In the summer of 2016, he performed at
Summerfest in Milwaukee opening for
Jason Derulo on the main stage. Throughout the year, he opened for a variety of acts including
Anderson Paak,
PartyNextDoor, and
Jeremih. In April 2017, it was announced that IshDARR had been cast as Steven "Freaky Steve" Roussell in the film,
White Boy Rick, starring
Matthew McConaughey. The film, which also featured IshDARR's brother BoodahDARR, had its wide release in September 2018. Later in April 2017, IshDARR released an EP,
Four The Better, which featured the singles "Free" and "Mucho Mango". Later that year, he again appeared at Summerfest, this time in a headlining role. His performance was recorded for the music video for his single, "Sanity". In 2018, he began releasing several new tracks, starting with "They Lost Me 2" and "Fangs" in January. He followed that with "Critical" in May and "Slow Down" in October. All of those tracks appeared on his mixtape,
Slow Down, KID, released in November 2018 and distributed by EMPIRE. A deluxe edition of the LP was released in April 2019 and featured 4 additional tracks. In March 2019, IshDARR was featured alongside his brother on the Royal Waev track, "Checks & Balances". He was also featured on the Saint Parrish track "Drown" ==Discography==