Car he learned to drive in
O'Neal grew up in the Roxbury area of Boston and didn't learn to drive until he was 22, in his mother's blue 1985 Chevrolet Citation. "My buddy had a license, so I would drive to his house up the block to go get him and we would drive all around the city," he says. "I would drop him home and drive back to my mother's house. That's how I got my first taste of driving."

Passing his driver's test was pretty easy, except for parallel parking. "I'm still not a good parallel parker. Nowadays with the backup camera, I really need that to help me out," he says.

O'Neal left Boston and moved to New Jersey, where he took the train, and when he later moved to Jersey City, mass transit abounded and having a car wasn't necessary.

"Then 9/11 happened," he says. "The trains started to run funny because of all the high alerts, so I ended up getting a car." He bought his first car, a 1995 Cadillac Seville with a white top, at an auction for $4000. By that time, he made some money from his half-hour Showtime and HBO specials.

"It was all red and it had the whitewall tires," he describes. "I loved it, but it was a Northstar engine and as soon as I bought it the head gasket blew. That's why I don't buy used cars anymore. My mother says, 'When you buy a used car, you're buying somebody's else's problems.'" That problem cost O'Neal another $4000 to fix.

First new car and used car karma
In 2004 O'Neal bought his first new car: a Chevy Suburban. "My credit was bad and my mother helped co-sign a car," he says with a chuckle. "My mom helped me co-sign a car in 2004! It was a Z71 package. I love that truck."

He added aftermarket wheels, which became a problem. "Of course I had to try to pimp it out a bit. And I started having a lot of problems with that!" he says. "It started tearing up the suspension and the stabilizer links. So I would take that to the shop all the time. But I loved that truck. That was a bad truck. It was gray but I had it painted black."

At that point he was a host for the VH1 show "Web Junk 2.0." "It was just me by myself on VH1. People knew me from that," he says. "I was getting paranoid, I thought people were following me. One night, me and my girl were driving around and I swear to God, somebody was following me with their lights off. I pulled up and stopped and they stopped behind me. I pulled up near a police station and they took off."

O'Neal soon traded in the Suburban for a 2007 GMC Yukon Denali, because he was worried people recognized his Suburban. "At that same time, my credit got good," he says. "So it served two purposes: It also cleared my mom for any responsibility for helping me out with her credit."

Even with good credit, he says he ended up getting what he calls "a dumb loan." "I got that on some no-money-down sh-t," he says, in a self-flagellating tone. "That was the first time I ever experienced having good credit and I did something stupid right out of the box!"

O'Neal says he then became part of the used-car karma game. "I felt the Yukon was going from something brand-new to used. You can feel the ignition was going a little, the ride was a little different, water was getting into the door when it rained. I got rid of it before the jig was up!" he says. "So I can tell you the used-car game is bad karma and I'm part of the bad karma, because I know that truck was going."

2010 Dodge Challenger R/T Classic
O'Neal traded it in for what he calls "a white guy's race car," a black 2010 Dodge Challenger R/T Classic "which was beautiful," he says wistfully. "I put a rear view camera, backup sensors in. It was a bad ride. I got a lot of compliments. It had the racing stripe, it had everything. Man!"

O'Neal tinted the windows and got stopped by the cops a few times. "I think the cops thought, 'What is this black dude doing in a white guy's race car?"

He also added a better sound system. "These Dodges don't have good sound systems," he says. "I need a little bass and I don't even need that crazy bass to break your face. I just want it to sound good when I have my favorite song."