A pressed Kenneth Cole shirt hangs next to him. Just a few more minutes in his ripped white T-shirt. He's going to tape "The Daily Show." It's the first stop in another jam-packed day, split into incongruent parts, each act showing a different side.
He looks at the buildings and the people and he remembers, laughing to himself. The first time he rode through these streets was 1994. He was more of a kid then, about 20. His daddy had won another Winston Cup championship and had come to New York for the awards banquet.
"I was f---ing out of my element," he explains. "I made the limo driver drive me around for a whole day looking at run-down f---ing places and hookers. I was like, 'I wanna see a hooker right now.' He'd drive there, 'There's one over there on the corner.' I'm like, 'Holy s---, a real hooker.'"
He's laughing at what a hayseed he was, and he's laughing at how far he's come in the five years since he was forced to become a star. The perpetual teenager has done some growing up, this year more than any other, struggling to move from where he was to where he wants to be. He's making progress on his journey, closer to the end than the beginning. He's 31. He owns a Busch Series team and a production company, just to name two. He hires and fires. He frets over rising gas costs.
"I think right now he's stepping out and showing he's his own man," best friend Josh Snyder says. "I think it took five years to get that confidence back. He did lean on his father for so much. That was taken from him. Now he's like, I'm trying to step up to the plate and be a man and do this on my own."
Junior is still immature enough to put a poker table where the dining table should be, but he is mature enough to contemplate his own legacy, even if he's not sure what it will be.
"You think I'm gonna get in the Hall of Fame?" he blurts, breaking the silence.
His publicist and friend, Mike Davis, turns from the front seat and says yes.
"Really?" Junior asks, surprised. "You think I've accomplished enough?"
"You're 22nd on the all-time list of wins already," Davis reassures him, referring to Junior's place on the Modern Era list (since 1972).
"Oh, yeah," Junior says.
He doesn't sound convinced, but any debate about his future will have to wait. They've arrived, on 51st Street. Sure enough, there's a crowd, shouting his name. Worlds collide on the sidewalk. There are racin' fans wanting diecast cars signed. There's a woman out there waiting to hand him a script.
He takes a breath and hums the theme of "The Good, The Bad and The Ugly," mentally slipping on his Wrangler-wearing rock-star public persona.
"My Clint Eastwood music," he says.
This is the Junior that fans don't get to see, the part of himself hidden by the swagger and backward ballcap. He is insecure sometimes, like everyone. Bravado is a coat he wears. He cares deeply about doing well, and this is one of the reasons he avoided adult responsibilities for so long. He's always wanted to please, and it seemed to bother him when he didn't. As a child, he painted elaborate models of stock cars. He took his time on each of them, but when he painted his father's car, the little boy bore down.
"I tried extra hard on his," he says.
What does that mean? Maybe nothing. Maybe everything. When he started racing, it would drive him crazy that his dad wouldn't praise him to his face. There was one driver who kept beating him, and Dale Sr. never let him forget that guy's name. Junior's won 17 Nextel Cup races, and he still remembers. He knows that the guy's still racing late models in South Carolina.
So for years, to protect himself against failure and disappointment, Junior acted like he didn't give a damn. He wouldn't start a Busch Series team; he wouldn't run the risk of not living up to expectations. He wouldn't admit to growing up.
"I think for a long time it was all really intimidating to me," he says, "and I didn't want to get into that stuff. Or I had a tendency to get involved in something and take such a lackadaisical approach as a defense mechanism in case it does bad or doesn't work out: 'Hey, it didn't mean anything.'"
He turned opportunities down. He acted a fool. All the while, life blew past.
"I probably would have done a few more award shows," he says. "I got invited to attend and present at the ESPYS and the [Country Music Awards], and stuff like that. I probably would have not turned those things down. I turned them down because I get stage fright."
He sips a Coke as he talks. Some of those issues are resolved, but he still gets nervous. It's close to show time. He sits in the greenroom, quiet, hands crossed, lips scrunched. Someone sticks his head in the door. Start your engines. They move through the halls, past "The Daily Show" offices, past Edit 1 and Edit 4.
Just offstage, Junior looks down.
"Back in 5 4 3 "
Less than 10 minutes later, he's done, back down the hall, out the door and into the Tahoe. There's a schedule to keep. Next stop: a helipad.
Junior is giddy. He watches Jon Stewart all the time.
"Man, I'm glad that's over with," he says, grinning. "I was nervous. He's just so f---ing good. It's like getting on a court with Michael Jordan. You're nervous you'd drop the pass or brick it. You just hope to not f--- the whole thing up. Man, that was awesome! There are certain things you remember doing. This is gonna be one of them. These are the shows of my generation. My friends are really gonna go, 'Jon Stewart!?'"
Please say, that if you hadn't of gone now
I wouldn't have lost you another way
From wherever you are come back
He looks out the window. The helicopter flies over a field of mausoleums. It's a familiar sight. His daddy is buried in one on family land, and when he's choppered to Lowe's Motor Speedway from his house, they fly right over it. It's as close as he wants to get. He stares down, makes sure the shrubs are pruned, that everything is perfect. He doesn't get overwhelmed by emotions; he's forced to deal with visions of his dad everywhere he goes. Later tonight, he'll be asked to sign a picture of his father, right below his father's own signature.
He's had to grieve in public. Five years ago, Dale Earnhardt crashed fatally on the last lap of the Daytona 500. The most enduring image is of Junior running down the track, trying to get to his father's car. It was like watching a man become a child again, the years slipping away with each stride.
"I honestly think that when his father died, his whole life changed in a matter of seconds," Snyder says.
Without his dad, he had to start over. Before that, Junior didn't really control his bank account. He didn't even have legal rights to his own name; the family business did. He made few decisions. Basically, he drove fast and partied hard. Life was simple.
That started to change in Turn 4. He felt it the first time he went to the Dale Earnhardt, Inc. shop afterward.
"When he was alive," Junior says, "people treated you like you were a punk. You knew at the end of the day, anything he said or did overrided your choices. I was doing whatever I was told. After he passed away I got treated as more of an adult."
That meant he had to act like more of one, didn't it? His decisions were made with dad in mind. He wondered if his fans liked him for him, or if they were just cheering for anyone named Earnhardt. Was he a success? Was he just the living reminder of an icon?
He searched for answers. His four straight wins at Talladega and his Daytona 500 win helped him begin to believe in himself. He noticed that people liked him, not just his father. Each moment was a step up in his five-year climb. He looked in the mirror and wanted more from life. His father had been a mogul. What was he?
"I think you get old enough to where it's like it's time to start acting a little more mature," he says. "Because if you continue to keep on playing the same card, people are like, 'Well, now not only is he not serious, but this is all he's going to make of himself.'"
So the journey began. Several years ago, he stopped going out after Tuesday night. He took more and more control of his affairs. He invested. He refused to be just another employee of DEI. Junior and Teresa Earnhardt, Dale's widow, had always had a complicated relationship, and soon after his dad died, he wanted it to be purely business with his stepmother.
"I think it took her a while to see that was my stance," he says. "I really don't go out of my way to spend a whole lot of time with her, and I rarely see her, so I think it took a while to understand, that's how he's gonna play it."
Last season, he began to make drastic decisions about his racing career. He let his longtime crew go. The moment he gave his OK was a line of demarcation. He felt like his own man.
His decisions didn't always garner results he had a poor season last year and is in danger of missing The Chase again but at least they were his decisions. Five years after he ran down the track, lost, he came to accept an important truth: Just because his father's legacy would always be there, it didn't have to define him. It's funny. Dale Earnhardt Sr. did exactly what he wanted. So the more Junior did things without his dad's posthumous approval, the more like his father he became.
"There's not a whole lot left to use as far as his experiences and his guide and what he would do," he says. "Now, it's like I can't remember what he would think about this. Now I've got to make a decision, and if it's f---ed up, I f---ed it up."
"What do you think the perception in the sport is after the press release?" he asks.
The day before, Junior had personally fired someone for the first time.
"Yesterday was the worst day of my life," he says.
The sponsors of his Busch team weren't happy with driver Mark McFarland and, finally, the team was out of options. Junior hates confrontation, but he called McFarland into an office and explained it to him. He knew his friend was sad, and he knew that he might be ending a dream. It's the most grownup he's ever felt.
"You better get used to that," Glynn tells him, as they decide on entrees.
"I hope I won't have to do that again," Dale Jr. says.
"That's business," Glynn says.
Junior shakes his head.
"I need to stop hiring my friends," he says.
He's learned a lot this year. He got his old crew chief back. Between producing television shows and running a team of his own, life's been hectic. He's handled it pretty well, though. That pleases the people who knew his father. So many NASCAR cognoscenti remember Junior as a child. That makes his continuing growth more special.
"There's another level of maturity," NASCAR president Mike Helton says. "Maybe it's just more experience."
If Senior were still alive, his son probably wouldn't be running a Busch team. Too much, too soon, he'd growl. But here Junior is, investing money, running race cars all over the freaking country, getting the phone calls every week that let him know how much more stuff his drivers tore up.
"Everybody runs that s--- over," he says, laughing. "They're like, 'F--- these guys; they've got all this good s---' and they wreck all my cars every week. I get a phone call: 'Hey, man, this is how much more f---ing in debt we are.'"
The biggest news came on June 17. He and his sister, Kelley, had been negotiating with DEI. He wanted the rights to his own name. Before his father died, he was in charge of all Junior's business, including copyrighting his name. After the wreck at Daytona, the rights to Junior's name transferred to his father's estate, then to Teresa. Junior wanted it back. After lengthy negotiations, it was done.
It took five years, but Dale Earnhardt Jr. legally was his own man. He was in his bus after practice when his sister called.
"You got the rights!" she told him.
He couldn't wait to get online and IM his buddies about it.
"I want it," he says. "It's my name. I want to feel like I'm not somebody else's. I felt like I was still being raised under her roof somehow, someway. So it was a way for me to really be on my own. That was the only reason. The others were business. I wanted to have it because it was rightfully mine and I could rightfully use it as leverage how I rightfully should be able to."
He knows what all this means, the taking on of responsibilities, the stepping out forcefully on his own. His Busch team, the late model stuff, the Hooters car, the radio show, the production company, all of it. If he doesn't make The Chase again this year, for the second season in a row, it's on him.
"Everything I do now, from here on out, where I end up is because of what I do now," he says. "It's cool, but it's scary and dangerous."
But enough with the business talk. They need to hurry up and make it to his public appearance tonight, plus the bride-to-be is finally coming over. There are certain things she'll remember doing. This is gonna be one of them. Her friends are really gonna go, "Dale Jr.!?" He's her Jon Stewart. She's a huge NASCAR fan (she doesn't know it yet, but her fiancÚ is about to give her two tickets to the race in Dover).
"You're Dale Earnhardt, aren't you?" she asks.
The screaming, already overpowering the sound system, gets louder when he turns his head. All the women in the place are convinced he's looking at them. There's an old bootleg of a Beatles show at Shea Stadium; barely audible beneath the shrieking and wailing is the actual music. This is like that.
There are, like, 2,000 people here (someone from the venue asked Junior's people for an autographed hat for the fire marshal). Junior's relaxed. He makes jokes about drinking in bars at Daytona. The crowd roars in response; he's like them. That's the attraction. He's accessible, more so, it seems, than others. For instance: There's a Web site that allows you to track private aircraft. Type in his plane's tail number N8JR and it will show where he is going. Now, type in, say, N24JG Jeff Gordon's tail number and it reads: "This flight is not available for tracking per request from the owner/operator."
Dale Earnhardt Jr. might own a Busch team, and he might want a future. But he will still hang with a bunch of good ol' boys and drink 'til the sun comes up. He might break into a friend's house and spread water and flour everywhere, you know, because it's funny. Ask him about the time he and some other drivers went to Panama City, Fla., and almost burned the place down.
"Nothing Budweiser would really be ashamed of," he cracks. "We got kicked off the pay ride go-karts. Went in the bars and danced our ass off with a bunch of girls."
Despite all his growing up, the old Junior is still beneath the business cards and adult transactions. He'll reach all his dreams someday. But right now, he's in the middle, no longer the boy he left behind and not yet the man he wants to become. He has more growing to do. The process hasn't ended.
When he had to address his employees after letting his driver go? He said he was hung over.
His pops called his yacht Sunday Money. Junior? He named his Sheezahooker and parked it in his mama's yard as a joke. (The smaller boat that goes with it is named Heezadinghy.)
He gets after it. Only now, when his boys call to see if he wants to throw down, he has to check his online calendar. If the next morning is free, and if it's before Wednesday, look out. He's got a boxing ring in his house, and, at his 30th birthday party got into it with Brad Arnold of 3 Doors Down, boxer Arturo Gatti and bull rider Ross Coleman. It was, like, 5 a.m. Arnold kept losing a contact, and Junior got laid out by Coleman. He had a black eye at that week's race.
"I still do s--- now that I would do when I was 25," he says, "and I'm like, 'Why the f--- did I do that?' You know, when I go raise hell until 9 o'clock in the morning, party all night. That damn Red Bull will get your ass."
There are all sorts of stories about his dad running rental cars ragged, wrecking four-wheelers and acting like an adolescent. One man burning up an engine is another man guzzling Red Bull. One man's Sunday Money is another man's Sheezahooker. Junior is the way he is for a reason. Rebellion flows through his veins. The crowd at the Long Island Irish bar loves that about him; everyone screams until he walks off the stage, down the stairs, into the night.
The show's finished. Everybody piles into a rental car. A fan runs out into the street, yelling incoherently. The trip to the Atlantic FBO at the Republic Airport in Farmingdale, N.Y., is short. His jet sits ready on the tarmac. Junior goes through the terminal and boards the plane. It screams down the runway, lifting off, headed toward Watkins Glen. He leans back and opens a book about shipwrecks and castaways. His day is almost over.
Tomorrow, he'll do it again.
Wright Thompson is a senior writer for ESPN.com and a contributing writer for ESPN The Magazine. He can be reached at firstname.lastname@example.org.