McEnroe retired from the professional tour in 1992, then used used his personality to entertain. He played host on a 2002 gameshow called "The Chair," which aired on ABC, and its British twin on the BBC. Contestants sat in a chair and tried to answer questions while having his or her heart rate monitored. If a player could keep their heart rate under control and answer seven questions, they could win a top prize of $250,000. "The Chair" lasted for just nine episodes on ABC, and only one contestant won the top prize.
In 2004, McEnroe played host to his own four-day-a-week talk show, "McEnroe," on CNBC. Guests included Elton John and Will Ferrell, and Patty Smyth sang the theme song, but the content never clicked with an audience. The short-lived series aired from July through mid-December, and the show twice pulled a Nielsen rating of 0.0 before it was cancelled.
McEnroe has made other television appearances, including spots on "Arli$$," "Suddenly Susan," "Frasier," "CSI: NY," "Curb Your Enthusiasm" and "30 Rock."
McEnroe also made several film cameos, first in 2002’s "Mr. Deeds." After Adam Sandler's character Longfellow Deeds goes on a bender, a mock TV celebrity anchor tells how Deeds "joined forces with the original bad boy of tennis, John McEnroe, and stupidity won in straight sets," as footage showed Deeds and McEnroe egging cars in New York City. A cab then careens down the street at McEnroe, and he jumps some 20 feet in the air to avoid the car. "What kind of driving is that?" he screams. "You're a f---ing disgrace!"
McEnroe went on to join Sandler again in 2008’s "You Don’t Mess with the Zohan," after his role in 2003’s "Anger Management" ended up on the cutting-room floor. He cursed at Sandler when the actor called to explain, upsetting McEnroe's wife, Patty Smyth. "Obviously, there is a funny side to your wife ripping you a new one because you couldn’t stop yourself from losing your s--- when your childish tantrum cameo got cut out of the film 'Anger Management,' " he wrote in "But Seriously."
In 2019, McEnroe's 1984 French Open final loss to Ivan Lendl was turned into a documentary called "John McEnroe: In the Realm of Perfection" by French filmmaker Julien Faraut. According to The Guardian, Faraut found uncovered courtside footage of McEnroe at Roland Garros in Paris and turned it into a story "about sport, film and the nature of genius."
"When you look back at old tennis matches, it’s always poor-quality video. Always the same boring edits, the same boring angles. But this felt dramatic, grainy, cinematic," Faraut told The Guardian. "When you focus on one man, it creates a kind of empathy."