The 1987 NASCAR Winston Cup Series Season was the 39th season of professional stock car racing in the United States and the 16th modern-era cup series. The season began on February 8 and ended on November 22. Dale Earnhardt of RCR Enterprises won the championship for the third time.
After a championship together in 1985, Darrell Waltrip decided to move from the No. 11 Junior Johnson Chevrolet to the new No. 17 Chevrolet, a third full-time Rick Hendrick-owned team.
A famous quote stemmed from this move, which crew chief Jeff Hammond describes in his book Real Men Work In the Pits went like this:
"I finally got me a thoroughbred." – Darrell Waltrip, referring to his new ride.
"I don't know about any thoroughbred. I do know we had a jackass around here who recently left." – Junior Johnson
The rest of "silly season" looked like this among full-time teams: Terry Labonte left the No. 44 Piedmont Oldsmobile owned by Billy Hagan to replace Waltrip in the No. 11. Johnson decided to disband the No. 12 Budweiser team and let go driver Neil Bonnett, who moved to the No. 75 Pontiac. Morgan Shepherd vacated the No. 75 in favor of the No. 26 Buick owned by Kenny Bernstein, driven by Joe Ruttman in 1986. Phil Parsons would replace older brother Benny in the No. 55 Oldsmobile owned by Leo and Richard Jackson. Lake Speed started out 1986 in the No. 75 RahMoc ride but was let go early in the season. Speed would form his own team for 1987 in the No. 83 Oldsmobile.
A few car number changes took place as well. Kyle Petty would continue to drive the Wood Brothers Ford, switching from No. 7 to No. 21. Alan Kulwicki took the No. 7 for his independent team. Cale Yarborough exited the No. 28 Ford team and drove his self-owned No. 29 Oldsmobile. Davey Allison would compete for Rookie Of The Year in the Harry Ranier No. 28 Ford.. Michael Waltrip would continue driving for Chuck Rider but switched from the No. 23 Chevrolet to the No. 30 Chevrolet.