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But after his annual Christmas party, he had too many trash bags and he let his neighbor dump them for him at his business. “He gets my truck and then he calls 30 minutes later, ‘Thomas. ‘ I was like, ‘Please, tell me nothing happened. ‘  He said, ‘You’re not going to believe this. ‘”

As his neighbor drove on the Houston freeway, out of the clear blue a deer runs across the road and into the truck. “When the insurance people took the car to get fixed, they fixed the whole thing, we lost the dent,” he says.

Dent or not, this is often Miles’ go-to car when he wants to feel his dad’s presence. “I get in and sometimes I just break down and cry and I can’t take it. I do it all the time,” he says. “I’m in my dad’s truck today, I’ve been hauling stuff around. I needed some firewood.”

Miles’ normal daily driver is a 2010 Rolls-Royce Ghost, which he also rates a perfect 10. “It’s a luxury drive, it’s so smooth, it glides. You feel like you’re on carpet. I like the way it looks; it’s so sleek, it’s regal. I like class,” he says.

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Most of the time he’s in the back seat, though. “My driver’s normally driving me around, especially if I’m going out and hanging out with the fellows, and the amenities in the back are just phenomenal. When you get in the car, you don’t have to pull the door to the little button, you hold and it closes it.”

His kids love the Rolls, as well, especially when it rains. “If it’s raining, inside the doors there is an umbrella on each side; you push a button, and the umbrella pops out,” he says. “The only thing that might be a dislike is it does draw a lot of attention, and sometimes you’re not really wanting all that attention.”

2009 Ford Flex

Rating: 8

Miles has this free Ford Flex in his garage thanks to his role on a nationally syndicated radio show. “I did a campaign on the radio for Ford a few years back, and not only did they pay me, but they also gave me a Ford Flex,” he says. “It’s been the daddy mobile where we load up, we go play baseball, football, soccer mom. It’s the diehard vehicle of the family. It takes care of everything.”

When Ford offered it, he took it. “They sent this car to this guy in New York, and he soups all these cars out. So when it was delivered to me in Texas, it had … rims on it, it had TVs in the headrest for my kids, it had an Xbox game in it, it had everything,” Miles says.

What he likes about the Flex is that it’s great for the whole family. “We’re all comfortable. When we’re on the road going out of town, whether to Galveston to the beach or to Dallas to some friends, it’s just a family-oriented vehicle where everybody’s got something to do the whole time in the car. Nobody’s bored,” he says. “I don’t think I have any dislikes about it. When you’ve got a free car, what’s there to dislike?”

Car he learned to drive in

Miles learned to drive on a tractor in Texas. “My uncle owned a land field, and at the age of 12 and 13, I was driving dirt and trash into a huge body of water,” he says. “I learned how to drive trucks, dump trucks, tractors.”

He officially learned on his mother’s canary yellow 1980 Cadillac Coupe DeVille.

“The kids used to tease me, ‘Look at the big banana Thomas is driving.’ But it was still a nice car, so I didn’t care,” he says. “I didn’t have a high school car—I had to have permission to drive my mom and dad’s car.”

His dad was his driving instructor who made sure to teach him how to drive properly. “His attention was always on driving, he was never lax on it … he was very thorough [and] made sure there were no mistakes,” Miles recalls.

That also meant Miles couldn’t make any mistakes, either. “If I got anything wrong while we were going around the block or something, then I didn’t get to drive the next day,” he says. “So I made sure I didn’t get anything wrong because he’d take a day off on teaching me.”

Much of those lessons were about being a good listener. “That’s what the whole lesson was, is to listen to what he’s saying, get it down, this is what we’re working on—the signal light, the way you ease up to a stop sign, instead of stopping abruptly,” he recalls. “He was just very thorough. So by the time I got to high school and the 10th grade, we could take defensive driving in school at 15, I had been driving already, for everything.”

First car bought

The first car Miles bought was a used Acura Legend from a fraternity brother. Although he can’t remember the model year, he remembers the car fondly.

“They don’t make those anymore. He sold it to me, and it was probably the worst deal I ever made because every two weeks I owed this guy 200 bucks, and that was a lot of money,” he says. “My father was like, ‘That was the dumbest deal you’ve ever done.’ But I liked the car, and he had it all nice with rims on it. I was like, ‘This is the best car, I’m never getting rid of it. ‘”

Miles made money from mowing lawns to pay for it. “Every morning I would get up and go pick up these laborers, they’d jump on the back of the trailer, we got lawn mowers, weed eaters, and we would cut 25 to 30 yards in one day,” he says. “That was my hustle. I toured with stage plays the majority of the time, but in the summer we were off. I would come home and I would run my cousin’s lawn service just to keep money coming in; that way I wouldn’t blow all my money that I made on the road while I was out performing.”

But after three years of paying his fraternity brother for the car, Miles had a tough time making payments. “He goes, ‘I’ll buy it back from you.’ And he buys it back from me, and it was so much cheaper than what I gave him,” he says.

Favorite road trip

Miles’ favorite road trip is the Pacific Coast Highway from San Francisco to Los Angeles, and not for the reason one would think.

“I just finished doing a comedy club in Oakland, and my road manager at the time said, ‘I don’t want to fly to L.A.’ I said, ‘Everybody talks about the drive up the coast; I want to drive up the coast. ‘”

His road manager found a rental, and they had a certain time they had to arrive and started on the drive. “He gets a nice SUV, a Tahoe, and I’m in a back with a pillow and a blanket, and I’m like a kid with all my snacks and goodies, and I’m like, ‘Yeah, we’re going up the coast!’ This was the scariest damn ride I have ever taken in my life. I could not believe all twists and turns. I’m looking off on the edge, I’m like, ‘There’s no barriers, there’s nothing that stops you from going over!'”

It was too late to turn around, so Miles made his manager drive 20 mph. “I don’t care how many people are behind us, damn it, drive slow! This is scary as all get out,” Miles recounts. “I had an appointment in L.A., I don’t give a damn, I called and cancelled the appointment, we are going to get there in one piece. We went through these little towns; I made him stop at rest areas so I could breathe. Just let me catch my breath and say, ‘OK, all right, I’m ready to go again, let’s drive another hour. Let’s get through this.’ I was terrified.”

He does recall seeing sea lions resting on rocks. “We saw all the good stuff that people want to get out, and I was like, ‘I don’t want a picture, just keep going, I’m good.’ That is the road trip that I will never forget—I thought it was beautiful, it was breathtaking, but it really did take my breath, though. It really scared the hell out of me,” he says with a laugh.

The Steve Harvey Morning Show and OWN’s Ready to Love

In addition to being the host on OWN’s Ready to Love show, Miles can be heard every morning from 6 to 10 a.m. ET on the nationally syndicated radio show as Steve Harvey’s co-host, where he’s known for his prank phone calls.

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He got the gig after he was touring with Luther Vandross. During a hiatus, he was asked to sit in on the show by Harvey’s manager.

“I’m like, ‘Hey, I’ve been doing this for a week now,’ and the next thing I look up, it’s two weeks and all of a sudden it’s like, ‘Steve wants to keep doing this.’ Are you serious? ‘I can do this for a while, but when Luther calls me I’ve got to go, I can’t be playing on the radio with y’all.’ The craziest thing is that Luther Vandross never went back out—during that hiatus time, he died. I look at it like God gave me a job before I even knew I needed one. And here we are 15 year later, and I’m still on the radio.”

Miles will always be grateful for that serendipitous moment. “This show has been far more than I could have possibly imagined. It has written my check for who I am today. I’m able to go and sell out venues across the country doing standup comedy because … people love who I am on that radio, and when they hear I’m coming to town, I’m sold out before I get there,” he says.

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He sees the show as a real blessing. “At first I didn’t take it serious, and then all of a sudden I started I realizing this is like a gift from God right here. I am able to do everything,” he says. “This past year I bought my wife a Bentley, and that’s what she rides around in. So I’m able to really give my family a whole different lifestyle because of this radio world that I live in.”

The Heckler

Miles is also producing and starring in the short film The Heckler, a dark comedy about a comic competing to win a comedy competition that could help pay for a costly bone marrow transplant for his dying son.

“He’s the best comedian in the competition, but on that night here comes the freaking heckler who kills every chance of this guy winning. But he finds out later that one of his best buddies who won the competition paid the heckler to make his show bad so he can win,” he says. “Everything hits the fan. It’s gritty and brutal and then there’s funny in between. … Look out for it because it will hit the film festival scene and you’re not going to be ready for it.”

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