2004-2008
In 2004, Menard began the NASCAR Busch Series season driving the No. 33 Menard's Chevrolet. Midway through the season, he moved to Dale Earnhardt, Inc. in the #1 Chevy. 10 races later, Menard won his first career pole position at Kansas Speedway and finished 23rd in points despite no top-tens and missing seven races. With Dan Stillman as crew chief beginning in 2005, they started out by leading 57 laps at Daytona. Winning the Bud Pole Award at Talladega also had them running up front until getting caught up in a wreck. He got his first top-10 and top-five by placing fifth at the Kentucky Speedway. From there, the team went from 20th to the top-10 in points before finishing sixth on the season.
In 2006, driving the #15 car part-time for DEI, Menard scored his first top-10 finish in the NEXTEL Cup Series by coming in seventh place at the Golden Corral 500 at Atlanta Motor Speedway. Menard also won his first Busch Series race on June 24 at his home track of the Milwaukee Mile by holding off a late race charge and bump from NEXTEL Cup regular Kevin Harvick. Harvick eventually caused a multi-car wreck attempting to bump him out of the way. Menard finished off 2006 with a sixth place finish in the standings, tying his best finish in the standings last year (2005). He scored 16 top-10 finishes and 7 top-5 finishes in the Busch Series.
In 2007, Menard ran his first full-time Cup season. He failed to qualify for six races that season, but after DEI's merger with Ginn Racing, the owner's points were transferred from Sterling Marlin's #14 car to Menard, who was then locked in to the rest of the races. His best finish of 2007 was in the Citizens Bank 400 where he finished 12th. In the Busch Series, he picked up 5 top-5 finishes. After the fall race at Charlotte, in which Menard and Tony Stewart made contact on pit road, a feud between the drivers ensued, with Tony Stewart (who drove for Menard's father John Menard in the Indy Racing League's early years) criticizing Menard's career, saying,
"You can have your father buy your ride and write DEI a big check, but you can't buy talent. And that's what John Menard's been good at his whole life, is just buying success. He's bought his son a Nextel Cup ride and he's just got enough talent to just be in the way most of the time."
In 2008, Menard won his first Sprint Cup Series pole at Daytona International Speedway in early July and remained in the top 35 in owner's points for the entire season. At Talladega in the fall, Menard had the best run of his career leading laps and coming home with a strong second place finish. He also was up front for a good part of the day in the other. He finished up the season with $3,559,130 in earnings and finished 26th in points standings, a career high. He has qualified for every race
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