1991 that he began being referred to in racing lineups as Michael (Waltrip). 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 TranSouth 500 at Darlington, but a jammed air hose on his final visit to the pits caused his stop to last 37.4 seconds, costing him the victory. 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 No. 21 Citgo-sponsored Ford. He won the 1996 edition of The Winston after capturing the last transfer spot in The Winston Open. After posting one top-five finish over three years, and missing his first race since 1986 at the 1998 Dura Lube/Kmart 500, Waltrip departed the Wood Brothers at the end of 1998 to drive the No. 7 Philips-sponsored Chevrolet for Mattei Motorsports, posting three Top 10 finishes and ending that season 29th in points. However, mid-season the ownership of the team transferred from Mattei to Ultra Motorsports and Jim Smith. The next season, Nations Rent replaced Philips as the sponsor & Waltrip moved up to 27th in points but only finished in the Top 5 once, causing him and the team to part ways at the end of the season. Waltrip would later say in his 2011 book, In the Blink of an Eye, that 1999 and 2000 were the most disappointing years of his racing career and he began to lose hope that he would ever win a Cup Series race. 2001–05 Waltrip was hired by Dale Earnhardt to drive his team's new No. 15 NAPA Auto Parts-sponsored Chevrolet Monte Carlo entry, Waltrip drove for Earnhardt in the Busch Series in 1989 and 1994. In his first race with the team, the 2001 Daytona 500, Waltrip broke his streak of 462 consecutive Cup races without a victory and won his first career points-paying Cup race. His teammate Dale Earnhardt Jr. finished in 2nd. However, the win itself was largely overshadowed by Earnhardt, Sr.'s fatal crash on the last lap. In the movie The Day: Remembering Dale Earnhardt, Waltrip said that Earnhardt let him in line late in the race, which allowed him to take the lead, noting that Earnhardt "never let anyone in line". This presumably is because Earnhardt wanted Waltrip and