Little Jackie isn't a single person so much as the second coming of singer-songwriter Imani Coppola. Coppola turned a few neo-soul-loving heads back in the late '90s in the form of a duo with her partner-in-vintage-beats, DJ/programmer Adam Pallin. While she was still just a sophomore in college, Coppola, the product of a musical family, recorded a demo with Digable Planets producer Mike Mangini that started a bidding war for her that Columbia eventually won. Her 1997 debut, Chupacabra, spawned the minor hit "Legend of a Cowgirl" and got Coppola a spot on Sarah McLachlan's Lilith Fair tour, but Columbia dropped her soon after (partially over her resistance to using samples, according to Coppola). Coppola spent the next decade as a struggling musician in New York, self-releasing her material for several years before getting picked up by Ipecac (which released The Black and White Album in 2007) and hooking up with Pallin as Little Jackie. S-Curve released the duo's debut, Stoop, in July 2008.