Jones was born in Mobile, Alabama. His father was a former professional baseball player for the Philadelphia Phillies. He moved to Mauldin, South Carolina, when he was a teen and graduated from Mauldin High School in 1985. One of his early acting experiences involved playing a werewolf in a haunted house to help raise money for the junior/senior prom. Jones enrolled in the College of Charleston, South Carolina. He left in 1990 without finishing his degree.

To pursue his interest in the entertainment industry, Jones, together with comedian Michael Fechter, formed a production company, Homeboy's Productions and Advertising. Together Jones and Fechter worked on several projects including a McDonald's commercial with basketball superstar Michael Jordan for the McDonald's specialty sandwich the "McJordan".

He scored his first Hollywood job in 1987, writing for the NBC comedy A Different World, on which he had a small guest role in the season five finale. During 1991-92, Jones penned the Fox series Roc and, in 1993, he co-produced The Sinbad Show. He also made a brief appearance on the FOX sitcom Herman's Head in 1992.

After hosting Fox's music series Sound FX, in 1994, Jones became one of the original nine cast members of MADtv. Unlike some of his fellow original repertory performers on MADtv, Jones came to the show with limited sketch comedy experience. However, his comedy writing and television producing skills proved to be valuable to the early success of the show.

Throughout Seasons One and Two of MADtv, Jones produced characters like the Cabana Chat band leader Dexter St. Croix and Reverend LaMont Nixon Fatback, the vocal follower of Louis Farrakhan. He was also noted for his impressions of Andre 3000, Bill Cosby, Dennis Rodman, O.J. Simpson, Samuel L. Jackson, and Snoop Dogg.

Characters

After two seasons on MADtv, Jones left the show at the end of its second season to pursue a movie career. However, Jones returned to MADtv in 2004 to celebrate its 200th episode. Jones appeared in the opening video "Hey MAD!" where he lampooned Andre 3000. With his guest appearance, Jones became the third (out of five) original cast member to return as a guest on the show. The other original cast members who have returned are Nicole Sullivan, Phil LaMarr, Artie Lange, and Debra Wilson.

During his time at MADtv, he roomed with Artie Lange, now a co-host on The Howard Stern Show. Orlando wouldn't allow Artie into the apartment if Artie had cocaine on his person. He was, however, according to Artie, very supportive and influential in helping to save Artie's life. Nicole Sullivan and David Herman of MADtv were also involved in the intervention (informing police and the show of his cocaine problem) of Artie Lange. This information was revealed on the June 12, 2006 episode of The Howard Stern Show on Sirius Satellite Radio by Artie Lange. Christa Miller, of The Drew Carey Show, was a roommate of Nicole Sullivan's at the time. Her appearance on The Howard Stern Show prompted Artie to reveal this information.

On July 28, 2008, Steve Langford of Howard 100 News reported that during the taping of the MADTV famous Babe Watch skit, Orlando claimed that when he awoke one morning, there was a horrible stench in the room and Artie was missing. Orlando said the bed was loaded with excrement. When house keeping came to clean the room he grabbed his stuff and jumped out the window to avoid being blamed. Artie Lange did confirm the incident.

Aside from MADtv, Jones made many other television appearances. Perhaps his most popular and enduring television appearance was not in the form of a sitcom or television drama, but rather in a series of humorous commercials for a soda company. In 2000, Jones became the spokesperson for 7 Up and he gained wide recognition.