8 Nov. 22, 1998
In a 300-plus mile exhibition in Motegi, Japan, Dale Jr. and Dale Sr. race each other for the first time. "Racing against him was always a dream," says Junior—who finishes sixth, two spots ahead of his dad.
7 July 2, 2010
Driving an Xfinity Series car with Senior's iconic number (3) and paint scheme (blue-and-yellow Wrangler), Junior wins at Daytona, breaking an 85-race drought. "Victory Lane's like when you're a little kid and you've got a treehouse or you and your buddies got a clubhouse in the woods," he says. "That's what Victory Lane is to me, and I like going there."
6 Nov. 15, 1998
Junior clinches the Xfinity Series title—in his first full season on the circuit—simply by starting at Homestead. "I wanted to get out after the first lap and get somebody [else] in there driving, so I could be celebrating," he jokes. (He was probably joking.)
5 Dec. 2, 2016
Despite missing half the season with concussion issues, Junior wins the fan vote as NASCAR's Most Popular Driver for the 14th year in a row (left). "It made the bad days better," he says of his roughest season.
4 May 20, 2000
Little E becomes the first rookie to win NASCAR's midseason All-Star race, passing several vets—including Pops (above). "I thought I could get up there and give [leader Dale] Jarrett some trouble," says Senior. "I looked in my mirror and here comes this red thing. I couldn't believe it."
3 April 2, 2000
In his 12th career start, Junior wins his first race, at Texas Motor Speedway (below), letting out a Lone Star State--sized "Holy s---!" as he crosses the finish line. Dad, a notoriously poor loser, comes in seventh but still beams. "He was pretty excited," says Junior. "He's the car owner too, so I guess he gets a cut of the check."
2 Feb. 15, 2004
Six years to the day after his dad won the Daytona 500, Junior takes the checkered flag at the Great American Race. He wakes up the next morning and promptly wins the rain-delayed Xfinity Series race, then hits the talk show circuit. On Letterman, he does burnouts in a Corvette outside the Ed Sullivan Theater.
1 July 7, 2001
Returning to Daytona for the first time since his father's death five months earlier, Junior dominates the night race (top), sewing up the win with a late pass on the same stretch of asphalt—the short chute between Turns 3 and 4—where Senior had been killed. "Shoot, I don't really care what happens after this," Junior says. "It doesn't get any better."