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American jockey

In the 2003 movie Seabiscuit, Stevens played jockey George Woolf, receiving generally positive reviews. He was recruited for the role in 2002 by the director, Gary Ross, and worked for four months on the film. In 2011 he became a regular cast member on the HBO television series Luck produced by Thoroughbred owner David Milch, starring as an on the skids jockey named Ronnie. The cancellation of the show in 2012 prior to the beginning of its second season turned out to provide Stevens with the inspiration to return to actual race riding. On January 12, 2013, Stevens won the first race of his comeback in a maiden race aboard the filly Branding. Stevens' first graded stakes win of his comeback came in the 2013 San Marcos Stakes on Slim Shadey. He reconnected with D. Wayne Lukas for the Triple Crown series on a horse named Oxbow. The team finished sixth in the 2013 Kentucky Derby, and on May 18, 2013, Stevens and Oxbow won the 2013 Preakness Stakes, his third Preakness win, and on the same day won the Dixieland Stakes on the undercard with the Lukas trained Skyring. After a second place finish in the Belmont, Stevens continued to ride regularly the rest of the year, and on November 1–2 at Santa Anita Park, Stevens won his third Breeders' Cup Distaff with Beholder as well as his first Breeders' Cup Classic aboard Mucho Macho Man. His Classic win was the first in 15 total attempts, and he was the only jockey to have ridden in both the first Breeders' Cup in 1984 and in the 30th in 2013. He finished the year 12th in the nation by earnings with 69 wins from 383 races and his lifetime wins total stood at 4,957. 2013 marked Stevens' third most successful year since 2000, comparing favorably to his 23 graded stakes wins from 487 starts and 94 wins in 2005 and 532 starts with 99 wins with 22 graded stakes wins in 2001. Coincidentally, in the same week, Mucho Macho Man was retired from racing, marking the second time a Stevens break coincided with the retirement of a horse he had ridden to racing success. Following surgery in late July 2014, he returned to riding in morning workouts in mid October 2014 and accepted mounts for the 2014 Breeders' Cup in the Juvenile Fillies Turf and Breeders' Cup Sprint.

Stevens' career as a jockey has been punctuated by a number of significant injuries. His first major accident was a starting gate training incident in 1985 when a horse threw him into the rail, putting him into a coma for 16 hours and causing serious injuries to his shoulder and right knee. In 2003, he suffered major injuries in the Arlington Million when his horse, in first place, spooked at the finish line, throwing him in front of the rest of the field, where one horse stepped on him, resulting in a collapsed lung and neck injuries. He returned to racing 19 days later. Over the years, he had gone through approximately a dozen medical procedures on his right knee and three on his left, mostly arthroscopic surgeries. In addition to his knee problems, he also had assorted surgeries on his right wrist and both shoulders. By 2014, his right knee required a total knee replacement. Medical testing revealed he also had been riding with a completely torn ACL. Following surgery, Stevens stated that he developed an addiction to the prescription painkillers he was given, so he isolated himself for a week and went off the medication cold turkey, after which he felt that he finally began to fully recover from the surgery. Three months after the operation, he returned to racing, working horses in the morning, and accepted mounts for the 2014 Breeders' Cup. He returned to graded stakes winning form with a Grade II win in the Grade II Arcadia Handicap on January 31, 2015:53 and achieved his 5,000th North American win on February 13, 2015. but indicated that 2017 might be his last year of racing, with the caveat, "unless I come up with a really good 2 year old who looks like he'll be a major contender for the 2018 Kentucky Derby." He returned to race riding on March 10, and rode a winning horse on March 11, 2017. Due to his multiple joint replacements, "The Bionic Man" became one of his nicknames.

On November 20, 2018, Stevens announced he was retiring as a jockey for good due to a neck injury that resulted from an accident at Del Mar on November 17. What was initially believed to be a pinched nerve turned out to be more serious. “[T]he C 4 is up against the spinal cord,” he said, “There won't be any comeback from this one.” He made the decision after doctors informed him that the spinal injury could lead to a far more serious issue if he were to ever fall again. In 2019, he returned to being a sportscaster, working as a racing analyst for Fox Sports.

Stevens has won numerous awards and prizes in the horse racing industry, including the George Woolf Memorial Jockey Award in 1996. In 1997, Stevens entered the National Museum of Racing and Hall of Fame and in 1998, he was voted the Eclipse Award for Outstanding Jockey in the United States. In 1999, he was voted the Mike Venezia Memorial Award. In 2003, he was a member of the first group of inductees to the Washington Thoroughbred Racing Hall of Fame. In 2013, he won the Big Sport of Turfdom award from the Turf Publicists of America, recognizing his contributions to the enhancement of Thoroughbred racing news coverage. He was also nominated for that year's Eclipse Award, and his contributions to the success of Mucho Macho Man were noted when that horse was the recipient of the 2013 Secretariat Vox Populi Award.