Born and raised in Newburgh, Maine, Ricky began racing at the age of 15 and has tasted success at every level of competition. His road to NASCAR NEXTEL Cup began at Unity Raceway in Unity, Maine with two wins and the Rookie of the Year title in 1982, followed by 12 wins and the track championship the very next year. Throughout the next few years, Ricky would earn wins at several tracks in New England before joining the American-Canadian Tour.

In 1989 Ricky made his first appearance in a major NASCAR touring series with his first Busch Grand National North start. Numerous wins, the Rookie of the Year title in 1990, two most popular driver awards, and the 1991 Busch Grand National North Championship set the stage for Ricky to move south to drive in the NASCAR Busch Series. Ricky continued his success by earning yet another Rookie of the Year title followed by consecutive runner-up finishes in the Busch Grand National standings. After 2 wins, 16 top 10's, and 8 top 5's in 1994, Larry Hedrick called on Ricky to drive his NASCAR NEXTEL Cup car for 1995.After an intense battle throughout the season, Ricky was named the 1995 NASCAR NEXTEL Cup Rookie of the Year, making him the first driver to ever earn the title in three major NASCAR touring series.

Additional rides in Ricky's NEXTEL Cup career including those with Hendrick Motorsports, SBIII Motorsports, and Midwest Transit Racing resulted in numerous achievements including several poles and a 3rd place finish in the 1997 Daytona 500 behind Hendrick teammates Jeff Gordon and Terry Labonte.

In January of 2001 Ricky was named to drive the No. 32 Tide Ford for PPI Motorsports and team owner Cal Wells. The results were instant, with the team recording a top 5 finish in only the second event of the season. The pairing culminated on October 15, 2001 when Ricky pulled into victory lane at Martinsville after holding off a last lap charge by Dale Jarrett to win the Old Dominion 500.Ricky's second season behind the wheel of the "Tide Ride" in 2002 resulted in a career best 15th place finish in the final NASCAR NEXTEL Cup Standings. PPI Motorsports announced an alliance with Pontiac for the 2003 season that paid immediate dividends as Ricky and the Tide team recorded their second career win at Darlington on March 16, 2003. Ricky edged Kurt Busch at the finish line by .002 seconds, the closest recorded finish in NASCAR history.

The next chapter in Ricky's career will be written in 2005 as he joins Roush Racing. Ricky will wheel the No. 99 Superchips Ford F-150 in pursuit of the NASCAR Craftsman Truck Series title for Ford and Jack Roush.