The Winston was created in 1985 by R. J. Reynolds, whose Winston cigarette brand was the title sponsor of what was then known as the Winston Cup Series. The inaugural event was held at Charlotte Motor Speedway on May 25, 1985 — the day before the Coca-Cola World 600 — and featured twelve drivers who had won races during the 1984 season. The race ran 70 laps with a mandatory pit stop and paid a $10,000 bonus to the leader of Lap 20; Terry Labonte collected that bonus.
The choice of name was deliberate and commercially significant. Because television broadcasting restrictions limited tobacco advertising, other Winston-sponsored races were referred to by generic names on network television — the Winston 500 at Talladega became the "Talladega 500," and the Marlboro 500 at Michigan became the "Michigan 500." The all-star event, however, had no generic alternative name, so broadcasters were required to call it "The Winston," effectively guaranteeing brand-name exposure on national television.
In 1986 the event moved to Atlanta International Raceway — the only edition not held at Charlotte — before returning to Charlotte in 1987 and remaining there for all subsequent editions through 2003.
The 1987 race introduced a new three-segment format and a new date — the Saturday before the Coca-Cola 600 — creating the two-week "Speed Weeks" local tradition at Charlotte. It also produced one of the defining moments of Dale Earnhardt's career. During the final ten-lap segment, Earnhardt was involved in aggressive contact that briefly sent his car through the infield grass at full speed. He rejoined the circuit and continued racing. The incident, known forever after as the "Pass in the Grass," became an enduring symbol of Earnhardt's combative, wheel-to-wheel racing style and elevated The Winston's cultural status within the sport.
The 1992 race was historic as the first superspeedway event held under artificial lights, marking the opening of the lighting system Charlotte Motor Speedway had installed that year. Davey Allison and Kyle Petty made contact on the final lap and crashed across the finish line; Allison was declared the winner but was taken to hospital rather than victory lane.
The 1994 running was the only Winston won on Hoosier tires rather than Goodyear, with Geoff Bodine claiming victory amid a contentious segment-two marked by multiple crashes including Ernie Irvan's wreck at the yellow flag.
In 1995, Dale Earnhardt debuted a special painted car that became a benchmark for the concept of distinctive one-off liveries at the event. In 1997, Jeff Gordon won in a car bearing a Jurassic Park: The Ride paint scheme, dubbed the "T-Rex." The car's aerodynamic characteristics were deemed sufficiently dominant that NASCAR banned it from further competition after the race.
Michael Waltrip's 1996 victory carried a unique distinction — he became the first driver to win The Winston after transferring into the main field from the consolation qualifying race. His win prompted a rule change that adjusted the procedure for how drivers could advance from the Open into the main event.
The event cycled through numerous race formats across its nineteen editions. The original 70-lap single-segment design gave way to a 135-lap three-segment format from 1987 to 1989 (75 laps, 50 laps, 10 green-flag laps), then a two-segment 70-lap layout from 1990 to 1991 (50 and 20 laps). From 1992 to 1997 the structure was three segments of 30, 30, and 10 green-flag laps. From 1998 the same 70-lap length was retained but all laps in all segments were green-flag laps only. In 2002, an elimination format nicknamed "Survival of the Fastest" was introduced, reducing the field between segments, before the race was restructured to 90 laps in its final two editions.
When Nextel Communications replaced R. J. Reynolds as NASCAR's title series sponsor in 2004, the event lost the Winston name and became the Nextel All-Star Challenge. The race continued at Charlotte Motor Speedway under successive title sponsorship names — Sprint All-Star Race, Monster Energy NASCAR All-Star Race — before eventually rotating to other venues from 2020. The format experimentation that had defined The Winston era continued under later sponsorship identities, cementing the event's role as NASCAR's annual laboratory for rule innovation.