Kulwicki claimed the ultimate prize - the NASCAR Winston Cup Series championship - in 1992, and Kenseth sits poised to lock up his title 11 years later.
But few similarities exist beyond those. Different backgrounds produced two contrasting personalities who took markedly different roads to the pinnacle at far, far different times in the history for the sport.
"Alan and Matt," says driver Mark Martin, "are not very much alike at all."
Kulwicki came from Greenfield, attended a Catholic high school, Milwaukee's Pius XI, and got his start in karting.
His father, Gerry, was too busy building engines for United States Auto Club stock-car racers to offer much help. Still Alan moved into cars, racing first on the dirt of tracks like the since-closed Hales Corners and Cedarburg speedways.
Simultaneously, Kulwicki attended the University of Wisconsin-Milwaukee, from which he earned a degree in mechanical engineering that helped him understand the physics of a racing car.
Kenseth, on the other hand, grew up in two small towns outside Madison, first Cambridge and later Rockdale. At age 13, he coaxed an agreement out of his father, Roy, that if Roy would buy a car and race, Matt would work on it until he was old enough to drive it himself.
When he was driving, Kenseth competed at places like Columbus and Jefferson, small local-level tracks not far from his home. And when he graduated from Cambridge High School, Kenseth went to work for Lefthander, a noted chassis-building business just south of the Wisconsin-Illinois border.
"Alan's approach was really unique," said Martin, a rival in both ASA and NASCAR. "Analytical. Went to college. It's more common today, but not nearly as common at all then.
"Alan was a very, very different person. Matt is just a hard-core racer. He's good at it, smart, real bright."
Kulwicki moved to asphalt, won titles at Slinger Speedway and Wisconsin International Raceway and competed in USAC and the American Speed Association. When Kulwicki made the decision to try NASCAR, he packed up his belongings and started a team of his own.
Kenseth claimed season championships at WIR and Madison International Speedway. He dabbled in the southern-based Hooters Cup late-model series and was just getting serious about ASA when Robbie Reiser offered him a ride in the NASCAR Busch Series. The influence of Martin, Roush Racing's lead driver, helped bring Kenseth into one of the largest teams in Winston Cup.
Coincidentally, the last Wisconsin stop for both Kulwicki and Kenseth was Gerry Gunderman's ASA shop in Franklin. And also coincidentally, Kenseth won the first Alan Kulwicki Memorial race at Slinger shortly after Kulwicki died in a plane crash in 1993.
"I don't know a whole lot about him and I never really met him and never got to know him," said Kenseth, 31, who was born nearly 18 years after Kulwicki. " . . . At 20 years old I was trying to race every week."
Kulwicki, the 1986 rookie of the year, made all the major decisions for his team, but the tiny organization of 15 beat the larger, established teams of Davey Allison (Robert Yates Racing) and Bill Elliott (Junior Johnson) to win the closest points battle in series history.
Kenseth, the top rookie of 2000, is one of about 30 people assigned to the No. 17 Ford, one of five Roush Winston Cup teams. The large leads he amassed brought cries throughout the season for a change in the points system. Going into the second-last race of the year Sunday in Rockingham, N.C., Kenseth holds an advantage of 228 points - more than a race's worth - over Dale Earnhardt Jr.
In 1992, Kulwicki picked up $2.3 million, including the $1 million champion's share of the $2.5 million points-fund money posted by series sponsor Winston. Kenseth has already won nearly $3.9 million and stands to add another $4,250,000 at season's end.
The television package NASCAR put together with Fox and NBC beginning in 2001 has helped draw new fans and resulted in a far greater audience than the one that watched 11 years ago.
"Money has changed. Obligations have changed, probably tenfold," said Tom Roberts, who was Kulwicki's publicist and who volunteered to help Kenseth early on as well. "It seems like week in and week out now, the champion or a group are going to New York or major-market areas for some publicity reasons, and 10 years ago the vast majority didn't know who they were talking about.
"The interviewers then had no earthly idea. Today it's changed to where these guys are such household names that in major market areas they at least know who you're talking about."
Some would say that Kulwicki's championship was more significant because of the way it was accomplished. Others might argue that Kenseth's stands out because NASCAR, on the whole, is a bigger deal nowadays.
"Don't ask me," Martin said. "I haven't managed it.
"It's quite an accomplishment."
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