How does a woman from St. Thomas, U.S. Virgin Islands, wind up in comedy? For Janelle James, it happened far away from that tropical paradise, at the University of Illinois at Urbana–Champaign. She went there to study pre-med. “But only because I didn’t know what to do,” she says. “Everyone needs a doctor. I always picked the hardest path.” Shortly after starting standup she dropped out of school. These days she headlines clubs across the country when she’s not featuring for Chris Rock. While she prefers headlining, being a middle has its advantages. “I’m a pretty good comic, you can put that in there,” she laughs, “but it’s a pretty cake position to be in, I think. Even if the fans are there for someone else and even if it doesn’t go well—and it usually does—they don’t remember you by the time the headliner comes out.” In her set, James mostly talks about personal experiences and how they impact her, such as auditioning for movie and TV roles. “It’s a demoralizing experience,” she tells an audience of what it’s like to gaze about the audition room. “You see all the different versions of yourself: if you were in shape, if you got enough sleep, if you never did drugs. Nine times out of 10, I’m the worst version of myself.” 18+.