Donnell Rawlings is a comedian with one of the rarest origins in comedy, evolving from a heckler to a celebrated performer. Before stepping into the world of stand-up, Rawlings served in the United States Air Force as a Military Policeman, with assignments in Washington D.C. and South Korea. After completing a four-year tour of duty, he planned to continue his career in law enforcement back in his home state of Virginia. However, a chance visit to a Maryland comedy club during an open mic night set him on an unexpected path. Initially attending a comedy show with his co-workers from a security job, Rawlings found amusement in heckling the new performers on stage. After several visits, the club owner challenged him to showcase his comedic skills on stage. Though the transition from audience to performer was not as easy as it seemed, Rawlings fell in love with the spotlight and decided to pursue comedy seriously. Within six months, his efforts led him to audition for the esteemed Def Comedy Jam. In 2003, Rawlings gained national recognition on the sketch comedy series “Chappelle's Show.” His connection with Dave Chappelle from the Washington D.C. comedy scene facilitated his participation, but it was Neal Brennan, the show’s co-creator, who recalled Rawlings from a previous audition for “In Living Color.” On "Chappelle's Show," Rawlings became widely recognized for his portrayal of the character Ashy Larry, as well as for the iconic phrase “I'm rich, biatch!” which capped off the show's episodes. This catchphrase subsequently inspired the “I'm Rich Biatch” comedy tour alongside fellow comedians Charlie Murphy and Bill Burr. After Chappelle's departure during the third season of the show, Rawlings co-hosted the "lost episodes" with Charlie Murphy, maintaining a strong presence and helping to preserve the show's humor. His stand-up career reached a milestone with the release of his first hour-long special, "From Ashy to Classy," in 2010. Throughout his career, Rawlings has credited his mother for his comedic sensibility, highlighting her ability to bring laughter into their lives despite financial hardships. Committed to reaching diverse audiences, he has sometimes forwent more lucrative opportunities to perform in venues that broaden his reach beyond the traditional black comedy circuit. Outside of stand-up, Rawlings has also made his mark in broadcast media, hosting morning radio shows in both Washington D.C. and New York City. His career trajectory, from heckler to headliner, exemplifies the transformative power of comedy and Rawlings' dedication to his craft.