Mike Tyson was supposed to make a cameo in DJ Jazzy Jeff & The Fresh Prince‘s 1989 music video for “I Think I Can Beat Mike Tyson.” Instead, the heavyweight champion took DJ Jazzy Jeff and Will Smith on an unexpected three-hour road trip through Ohio, leaving an entire film crew wondering when their stars would return.
During an exclusive 2020 interview with Chad Kiser, DJ Jazzy Jeff recalled the unusual experience of recruiting Tyson and boxing promoter Don King for the music video, which accompanied the duo’s third studio album, And in This Corner…
By the late 1980s, Tyson was one of the most recognizable athletes in the world. The undefeated heavyweight champion had built a fearsome reputation through his devastating knockouts, while DJ Jazzy Jeff & The Fresh Prince were enjoying mainstream success following their Grammy-winning single “Parents Just Don’t Understand.”
The idea for “I Think I Can Beat Mike Tyson” grew out of conversations about people who believed they had figured out how to defeat the seemingly unbeatable boxer.
Jeff explained that he and Will had known Tyson since his early career, when the young fighter would attend their performances at New York’s legendary Latin Quarter nightclub.
With that relationship already established, they decided to ask Tyson to appear in the video.
There was just one problem: Tyson wasn’t exactly known for following other people’s schedules.
According to Jeff, plenty of artists wanted the champion in their music videos, but getting him to actually show up was another matter.
To improve their chances, the production was arranged in Ohio, where Tyson was living at the time. Even then, Jeff worried that the boxer might never arrive, leaving the crew without the video’s biggest guest star.
Fortunately, Tyson showed up.
But instead of immediately getting to work, he had something else in mind.
“Hey, jump in the car, I want to show you something,” Tyson told Jeff and Smith.
The two climbed into Tyson’s car, and what might have seemed like a quick trip turned into a three-hour excursion through Ohio’s Amish country.
Tyson was having a house built and wanted to show it to them.
Back on the set, the production crew could do little but wait.
Jeff recalled that they were gone for approximately three hours, leaving the crew unsure what to do. After all, nobody was particularly eager to tell Mike Tyson that he needed to hurry back to work.
Eventually, the trio returned, Tyson put on the boxing gloves, Don King arrived, and the video shoot was completed.
The finished clip featured Smith stepping into the ring against the heavyweight champion, combining the duo’s trademark humor with one of the biggest personalities in professional sports.
The song appeared on And in This Corner…, released in October 1989, but its timing would soon become an unexpected part of the story.
On February 11, 1990, Tyson suffered one of the most shocking defeats in boxing history when James “Buster” Douglas knocked him out in Tokyo, ending his undefeated streak and reign as heavyweight champion.
Jeff remembered the timing as particularly unfortunate for a record built around the idea of defeating Tyson.
“It was awkward!” he told Kiser.
More than three decades later, the story remains an entertaining reminder of an era when hip-hop, professional sports, and popular culture were becoming increasingly intertwined.
For DJ Jazzy Jeff and Will Smith, what began as a humorous concept about challenging the world’s most feared boxer became a memorable collaboration with Tyson himself—and an unscheduled three-hour road trip that the production crew probably never forgot.
The story was one of several behind-the-scenes revelations from Kiser’s extensive 2020 conversation with Jazzy Jeff, which also covered Dr. Dre‘s involvement in Straight Outta Compton, the creation of “Summertime,” Will Smith’s early battle-rap background, and the duo’s recording history.
Read my complete DJ Jazzy Jeff interview: