Grissom had four top-tens in the 1995 Cup season, finishing 27th in points; he started the season running in the top-10 points early on in the year. Grissom started 1996 off on a high note, winning the season-opening Busch Series race driving the WCW car, but he was released from Diamond Ridge after the Miller 400 race midway through the season. For 1997, Grissom signed on with Larry Hedrick Motorsports. Grissom started the year winning the outside pole for the Daytona 500. As the season progressed, he finished in the top-ten six times and finished a career-high 21st in points. After he struggled throughout the 1998 season, he was released from his ride and ended the season driving the No. 96 for American Equipment Racing. Grissom's No. 41 Chevrolet had a major crash during the Primestar 500. Grissom's car slid into the inside wall and flipped on the roof. The gas tank was detached by the impact, which flew across the racetrack, spilling gasoline. Which later ignited a fire by friction with Mike Wallace's car. Grissom was taken to the infield medical center, and released 45 minutes later. The fire was extinguished and the racing resumed about an hour later with 44 laps remaining. After American Equipment closed its doors, Grissom started the 1999 season with LJ Racing in a four-race deal. After his contract was not renewed, he spent the season doing fill-in duty for Carroll Racing, Travis Carter Motorsports, and Hensley Motorsports, among others. In 2000, Grissom was hired by Petty Enterprises to drive their No. 43 Dodge Ram in the Craftsman Truck Series. This year was best known as when Tony Roper turned into Grissom's bumper and hit the wall head-on at Texas Motor Speedway, then hitting Roper's truck as it slid down the track. Roper died of injuries he sustained from the crash the next morning. While he did not visit victory lane, Grissom finished in the top-five six times and finished tenth in points. He also ran in the Cup series, filling in for Kyle Petty in the No. 44 Hot Wheels Pontiac Grand Prix. After spending virtually all of 2001 on the sidelines, he was called back to Petty in 2002 to replace Buckshot Jones in the No. 44. In ten starts, he posted one top-ten at Richmond International Raceway. He has not run a Cup race since. That season, Grissom ran seven Nationwide