The Comedy Repertoire of Orlando Jones

Actor, writer, and comedian Orlando Jones joined The Preston & Steve Show this morning, and if you’ve ever wondered what it’s like to juggle acting, writing, and working with some absolute Hollywood legends, Jones had plenty of stories to share. He was also calling in to promote his upcoming show at City Winery on March 23rd.

Orlando has worn a lot of hats over the years, including running his own music label and writing comedy for some of the biggest names in entertainment. He told the gang that when he was deep in writing mode, he had pens, paper, and recorders everywhere because ideas would hit constantly and he needed to capture them immediately. If a joke popped into his head, he was writing it down.

Steve asked about working with comedy legends like Harold Ramis and whether he was able to learn from people like that along the way. Jones said absolutely. Being around talented performers and writers helps shape how you approach comedy, especially when you’re writing for someone else. He explained that writing for another comic is all about matching their rhythm. The tone, delivery, and timing have to feel natural for the person performing it.

Jones also broke down how precise stand up comedy can be. The order of jokes matters, the positioning of a bit within a set matters, and execution is everything. Sometimes the toughest part is resisting the urge to fall back on material you already know works instead of pushing yourself to create something new.

Of course, working in Hollywood means some pretty great stories. Jones talked about working with Gene Hackman and immediately trying to joke around with the legendary actor on the first day of shooting. Jones walked over and asked him if he was really “going to do it like that.” Hackman didn’t respond and just walked away. Later, after Jones finished his take, Hackman walked over and joked that his replacement was on the way. Safe to say the sense of humor was mutual.

He also worked with Keanu Reeves right after Reeves finished filming The Matrix. Around that time Jones was doing double duty on a project, acting and writing at the same time. He said they were filming around 150 pages a week and he occasionally slept in his dressing room just to keep up with the workload. At one point he was the only cast member who was also writing for the show.

The conversation also turned to his longtime friendship with Artie Lange. Jones said they still stay in touch and described Lange as being like a brother to him.

Sports came up as well, which makes sense considering Orlando Jones’ family background. His father actually played for the Philadelphia Phillies around 1967, making Jones the only guy in the family who didn’t go the professional athlete route. When he told everyone he was moving to Los Angeles to pursue acting instead of sports, the family literally held a meeting about it. Jones said if he had followed the sports path, basketball would have been his choice. He’s a big fan of the Philadelphia 76ers and even played in the NBA Entertainment League alongside celebrities like Kevin Hart.

Eventually things worked out pretty well for him. Jones said buying his parents a house was his personal “how do you like me now” moment after all the questions about moving to LA.

Jones also talked about popping up on Abbott Elementary after creator Quinta Brunson reached out while she was trying to get the show off the ground.

There is also one wild behind the scenes story from his time on the film Bedazzled you certainly don't want to miss. It made our jaws drop: