The Harlem-raised rapper Max B's career is bookended by spells in jail. After serving an eight-year bid for robbery, he hooked up with Jim Jones and began an association with the uptown crew Dipset. That move included a co-starring role on Jones's smash "We Fly High"—until the two artists entered into a beef that led to Max B retreating to the mixtape scene on his own terms. While readying his studio debut, he fell foul of the law again and was sentenced to 75 years on a murder charge. His album Vigilante Season dropped while he was inside.