Rawlings was born in Washington D.C. and grew up in Alexandria, Virginia. He grew up with his mother. Rawlings attended T.C. Williams High School in Alexandria, Virginia. He served in the United States Air Force stationed in South Korea and as Military Police on Bolling Air Force Base in Washington, D.C. in the late 1980s and early 1990s.
Rawlings is most notable for frequently appearing in sketches on Chappelle's Show and hosting the third season along with Charlie Murphy. His catchphrase on the show was "I'm rich, biaaaaach!" (which is played at the end of every episode as part of Dave Chappelle's vanity card) as well as frequently adding "Son!" at the end of each sentence.
He demonstrates his knowledge of the broken Korean he learned in the Air Force in the Chappelle's Show sketches "Player Hater's Ball" and "The Time Haters", the latter of which was featured in the "Failures" episode. Rawlings reprises his role as the hater "Beautiful", known for wearing a Jheri curl and a suit similar to ones that Little Richard has worn. In the sketches, he responds to the comments of Korean hater "Mr. Roboto" with insults in Korean.
Rawlings stars in a series of sketch comedy clips portraying his character Ashy Larry, from Chappelle's Show, on heavy.com called "From Ashy to Classy". Ashy Larry dreams of how his life would be if he were classy, and dreams up a character who he calls Ashford Lawrence, a supposed reporter for heavy.com. Ashy Larry goes to different high class establishments posing as a reporter, where eventually his girl comes and pulls him out at the end of each clip.
Rawlings also made appearances on the HBO drama The Wire playing Damien Lavelle 'Day-Day' Price, an ex-convict who is hired as a legislative aide and driver for corrupt state senator Clay Davis. Price's character appears unrefined on several occasions contemplating heists in public and stating things in the court room such as "Y'all tryin' to 'criminate me" while on the stand. Davis coincidentally enough is played by Chappelle's Show co-star Isiah Whitlock, Jr.
Rawlings appears in Sam Raimi's Spider-Man 2 and a cameo appearance in the music video for Jim Jones' "We Fly High" (Ballin' Remix). He was a regular on The Ricki Lake Show mostly as a Judge on Various challenge episodes.
In summer 2007, Rawlings was featured on the cover of the one-year anniversary issue of Beyond Race magazine. Rawlings was removed from his morning show post at Power 105's Ed Lover Show with Egypt and Ashy for a controversial comment the comedian made during the aftermath of the Don Imus controversy, responding to Ed Lover's comment "That's a cheap black man, Nickel-Black" with "that's a Jewish black guy."
Rawlings was also a contestant in the Comedy Central show Reality Bites Back. He appeared in sketches on D.L. Hughley Breaks the News and in Howard Stern's Howard TV On Demand original series, Show in the Hallway.
In July 2009, Rawlings recorded a clip imitating Stephon Marbury crying on his live webcast. Rawlings was a co-host on the Big Tigger Morning Show on Washington, D.C.'s radio station WPGC 95.5 from April 2010-January 2011.
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