Craven began racing at fifteen at Unity Raceway in Maine, winning twice and taking the Rookie of the Year award in his first season. He went on to claim the Busch North Series championship in 1991, winning ten times in the No. 25 Chevrolet. He was also named Rookie of the Year in the Busch Series in 1992 after moving to full-time competition there, finishing second in the championship standings in both 1993 and 1994.
Craven made his Winston Cup debut at Rockingham in 1991, starting and finishing 34th for Dick Moroso. In 1995 he joined Larry Hedrick Motorsports and Kodiak to run for Winston Cup Rookie of the Year, qualifying for all 31 races, scoring four top-ten finishes, and beating Robert Pressley for the award.
In 1996 Craven suffered a frightening crash at the Winston Select 500 at Talladega when his car was launched into the air and impacted the catch fence before being thrown back onto the track. He walked away but the incident affected his season. He then moved to Hendrick Motorsports to drive the No. 25 Budweiser Chevrolet, finishing third in the 1997 Daytona 500 behind teammates Terry Labonte and Jeff Gordon — giving Hendrick Motorsports a 1-2-3 sweep of the race.
During practice for the inaugural Interstate Batteries 500 at Texas Motor Speedway in 1997, Craven crashed hard into the wall and suffered a concussion. He missed two races but returned to finish nineteenth in points for the year. When the 1998 season began, side effects from the concussion resurfaced and he was diagnosed with post-concussion syndrome, forcing him to miss several more races. He was ultimately released from Hendrick Motorsports and did not return to full-time competition until the following season.
After struggling with underfunded teams in 1999 and 2000, Craven joined PPI Motorsports in 2001 to drive the No. 32 Tide Ford. That year at Martinsville Speedway he held off Dale Jarrett late in the Old Dominion 500 to score his first career Winston Cup victory. In 2002 he won two poles, posted nine top-ten finishes, and achieved a career-best 15th-place finish in the championship standings.
In 2003, PPI switched from Ford to Pontiac. At the Carolina Dodge Dealers 400 at Darlington Raceway, Craven and Kurt Busch waged a side-by-side battle over the final laps. Craven prevailed at the finish line by just 0.002 seconds, a margin that was voted the "Finish of the 2000s" in the Sprint Cup Series in a December 2009 poll. With that win, Craven became the last driver to win a Cup race in a Pontiac. The 0.002-second margin stood as the closest in Cup Series history for more than twenty years, eventually surpassed by Kyle Larson's 0.001-second margin at Kansas in May 2024.
After failing to record a top-ten finish three-quarters of the way through 2004, Craven was replaced and did not return to the Cup Series until a one-off run at Talladega that year in a development car for Joe Gibbs Racing. He moved to the Craftsman Truck Series in 2005 with Roush Racing, running second in points after nine races before falling back, eventually winning at Martinsville and finishing fourteenth in points. His final NASCAR start came in the 2006 Busch Series Goody's 250 at Martinsville for FitzBradshaw Racing, where he retired after brake failure.
After retiring from driving, Craven joined ESPN and Yahoo! Sports as a NASCAR analyst. He worked for ESPN for twelve full years before departing in January 2019 to join Fox Sports, where he remained through the 2020 season. In 2025 he purchased Speedway 95 in Hermon, Maine, renaming it Ricky Craven Speedway.
Craven's 2003 Darlington victory remains one of the most celebrated finishes in NASCAR history. His career is also notable for his perseverance through the post-concussion syndrome that threatened to end his driving days prematurely, and for his emergence as a respected analyst and broadcaster after stepping away from the car.