Trickle was born in Wisconsin Rapids, Wisconsin, and fell in love with racing after attending his first event at Crown Speedway as a nine-year-old, during a lengthy recovery from a hip injury sustained in a childhood fall. His family lived on welfare and there was no money available for racing; he spent his teenage summers working for farmers and at his father's blacksmith shop, saving scrap metal and parts to eventually build his first race car. At sixteen he bought a 1950 Ford for $100 and cut it up to create a stock car. From that improbable beginning, Trickle built one of the most extraordinary careers in American short-track history.
Trickle raced over one hundred events a year for more than fifteen years on the tracks of central and western Wisconsin. He won 67 races in 1972 alone — the season that established him as the winningest short-track driver in the country. In 1971 he raced on the Central Wisconsin Racing Association circuit nearly every night of the week, winning on Wednesday at La Crosse, Thursday at State Park Speedway, Friday at Capitol Speedway, and Saturday at Wisconsin Dells Speedway. He held track records at six circuits simultaneously.
He won seven ARTGO Championships in nine years between 1979 and 1987 and captured back-to-back ASA AC-Delco Challenge championships in 1984 and 1985. He also won the USAC Stock Car Series Rookie of the Year award in 1968. Of all his victories he considered the 1983 World Crown 300 in Georgia his most satisfying win — a result that required three weeks of preparation and yielded a $50,000 payday that was the biggest of his career to that point.
Through the 1970s and 1980s, Trickle made sporadic Winston Cup appearances, including three Daytona 500 starts. He famously resisted Bill France Sr.'s personal invitation to join the series full-time, quipping that he "didn't want to take the pay cut" from his highly successful short-track earnings.
In 1989, at 48, Trickle made his full-schedule Cup debut driving the No. 84 Miller High Life Buick for Stavola Brothers Racing, having replaced the injured Mike Alexander. Despite never winning a Cup race — he was also a grandfather at the time — his racecraft and public personality made him an immediate fan favorite. Upon accepting the Rookie of the Year trophy, he joked: "I guess I'd just like to thank everyone who gave a young guy like me a chance." His best Cup career finish was third, achieved five times, across 303 starts with 15 top-fives and 36 top-tens.
In 1990 Trickle won the Winston Open — the non-points qualifying race for The Winston — by 8 inches over Rob Moroso, and claimed his only career Cup pole at Dover Downs International Speedway. He was well-known for having drilled a hole in his safety helmet to allow smoking during caution periods, and NASCAR permitted him to light a cigarette during yellow flags. In 1990 he was captured on live television doing exactly this via the in-car camera during the Winston 500.
He also competed in the Busch Series, winning two races in 158 career starts. After leaving full-time Cup competition he continued racing occasionally in Wisconsin events, including the 2001 and 2007 Slinger Nationals.
Trickle's name generated consistent media attention. ESPN anchors Dan Patrick and Keith Olbermann made a point of mentioning his finishing position during NASCAR SportsCenter highlights. The main character of the 1990 film Days of Thunder, played by Tom Cruise, is named Cole Trickle as a direct homage. In a 1997 NAPA Auto Parts television commercial, Trickle himself played up his winless Cup record humorously, noting on-screen that he was "0 for 243 in Cup races."
Multiple Wisconsin short tracks have established Dick Trickle memorial races, typically run at 99 laps to honor his car number. La Crosse Fairgrounds Speedway created the Dick Trickle Classic in 2007 and has hosted the event annually since. Wisconsin International Raceway named a building in turn two the "Dick Trickle Pavilion." A memorial at Rudolph Community Park was organized by friends and former competitors. Former rival Rusty Wallace credited Trickle as his mentor: "Between Larry Phillips and Dick Trickle, they taught me everything. My success in the ASA and what Trickle taught me is what got me into NASCAR."
Trickle died on May 16, 2013, from an apparent self-inflicted gunshot wound at Forest Lawn Cemetery in Boger City, North Carolina. His family later disclosed that he had been suffering from severe chronic pain for some time, for which doctors had been unable to find the source. NASCAR chairman Brian France called him "a legend in the short track racing community" whose personality "helped shape our sport."