Waltrip's stock-car career got off the ground in 1981, when he captured the Mini-Modified division track championship at Kentucky Motor Speedway. A year later, Waltrip entered the Goody's Dash Series, where he won the series championship in 1983 and was voted the circuit's most popular driver in 1983 and 1984.
In 1986, driving the #23 Hawaiian Punch car for Bahari Racing, Waltrip finished second in the Cup rookie of the year race to Alan Kulwicki on the strength of a pair of 11th-place finishes at Martinsville and Pocono. The following season, he posted his first career top-ten finish when he ended up tenth in the spring race at Martinsville Speedway. In 1988, Waltrip began running Busch Series events, making five starts for his brother Darrell's fledgling team. He took the checkered flag for the first time at Dover in his fourth start. In 1989, he had his first top-five finish in the #30 Country Time Lemonade/Kool Aid Pontiac. 1990 was remembered for a horrific crash at Bristol in the spring where Waltrip destroyed his Pontiac. Waltrip only suffered bruises in the incident. The accident was referenced in a 2008 NAPA Auto Parts commercial, where a fan showed Waltrip his customized die-cast replica cars, including pieces of the 1990 Bristol car. In early race lineups he was referred to as "Mike Waltrip" or Darrell's little brother, it wasn't until 1991 that he began being referred to in racing lineups as Michael.
In 1991, he gained new sponsorship from Pennzoil and won the Winston Open, as well as his first two career pole positions. He came close to winning the 1991 Southern 500 with the team but had an incident that put him out of the running. Waltrip would have to wait 10 more years to get his first win. He stayed with the Bahari team until the end of 1995, when he was replaced by rookie Johnny Benson. He joined Wood Brothers Racing to drive their #21 Citgo Ford. He won the 1996 edition of The Winston . After posting one top-five finish over a period of three years, and missing his first race since 1986 at the 1998 Dura Lube/Kmart 500, Waltrip departed the Woods at the end of 1998 to drive the #7 Philips Chevrolet for Mattei Motorsports, posting three top-ten finishes and ending that season 29th in points. The next season, NationsRent replaced Philips as the sponsor & he moved up to twenty seventh in points but finished in the top-five once, causing him and the team to part ways at the end of the season.
In 2004, Waltrip went winless and dropped five spots in the standings. Despite one pole and seven top-tens in 2005, Waltrip announced he and sponsor NAPA would depart DEI to drive the #55 Dodge Charger for Bill Davis Racing. After the former #77 Jasper Motorsports team closed its doors at the end of 2005, Waltrip split unofficially from Davis and assumed the former Jasper team's owner's points in order to be guaranteed a spot in the first five races for the season. Running under the banner, Waltrip-Jasper Racing, the team would be used to set up Waltrip's new Toyota operation in 2007. Waltrip failed to qualify for the first time since 1998 at the Coca-Cola 600, he bought a slot from the #74 McGlynn Racing Dodge from Derrike Cope to drive in the race and to keep his streak of 262 consecutive races. Waltrip ended up missing three races total in 2006 and did not have a top-ten finish.
On Saturday April 7, 2007 he fell asleep behind the wheel of his Toyota Land Cruiser which overturned and struck a utility pole. Michael crawled out from the car suffering only minor cuts. There was no Nextel Cup race held that weekend. He was charged with reckless driving and failing to report an accident.
After failing to qualify for the Pocono 500 in June, Waltrip bounced back the following week by finishing 10th at the Citizens Bank 400 in Michigan.
On October 6, 2007, Michael won the pole for the UAW-Ford 500 at Talladega Superspeedway, the first restrictor plate race to be run with the Car of Tomorrow. He finished 25th after a wreck, but bounced back the next week at Lowes Motor Speedway with his second top-10 finish of the season.
In 2008, Michael Waltrip Racing underwent a change following the disappointing 2007 campaign. Waltrip welcomed business owner Robert Kaufmann, owner/founder of the Fortress Investment Group and was made an equal partner and got more aid with real estate developer Johnny Harris buying into the team during the 2007 off-season. Former Cup owner Cal Wells III also bought into the team. The name also underwent a change as it now operates as Michael Waltrip Racing Holdings LLC. On February 10, 2008, Michael qualified second for the 50th running of the Daytona 500, which guaranteed him a second place start in the race. After making his first pitstop, he gave his personal "Gold Tires" that he was running on his car that he started the race with and he gave to a fund. After leading the first two laps, he was not a factor in the race and finished 26th. Waltrip finished second at New Hampshire's Lenox Industrial tools 301.
In 1995 at Michigan International Speedway, Waltrip again lashed out at a fellow driver, this time Lake Speed. Waltrip struck Speed twice on national television, while Speed was still strapped in his car. Waltrip was fined $10,000 for his actions.
Waltrip had a much-publicized feud with Jeff Green, then driver of Petty Enterprises #43 Cheerios/Betty Crocker Dodge Charger in the early part of the 2005 season, which came to a head during races at Martinsville and Darlington, where Green and Waltrip wrecked each other on several occasions.
In the 2005 Sylvania 300, Waltrip wrecked Robby Gordon's #7 Jim Beam Chevrolet after the yellow flag had come out. The angered Gordon got out of his totaled car and threw his helmet at the #15 car as it was passing by. When TNT interviewed him about the crash he stated "You know Michael, everyone thinks Michael's just this great guy, but he's not the good guy he acts he is. The caution was out and he wrecked me; and he's a piece of shit. On the next caution lap around, some viewers claimed that Waltrip flipped Gordon the finger as he drove by, although subsequent video replays are inconclusive and Waltrip denies making the gesture. TNT apologized for the incident on both driver's behalf, and both Gordon and Waltrip were required to meet with NASCAR officials after the race. Gordon was fined $50,000 and docked 50 drivers' points. Waltrip was also penalized, but the penalties were overturned on appeal. Gordon ultimately decided to auction the helmet for the benefit of the Harrah's Employee Relief Fund, a fund that provides aid to Harrah's employees displaced by Hurricane Katrina. Both drivers signed the helmet, which was purchased by GoldenPalace.com for $51,100.
Best Western and Michael Waltrip Racing in Search of Stock Car Racing's First-Ever "Official Tweet Crew Team".
Feb 06, 2010; The World's Largest Hotel Chain[R], Best Western, has teamed up with Michael Waltrip Racing to conduct a national job search for...