On Friday, July 21, 2023, the world lost one of the most revered, legendary talents in music history, Tony Bennett, at the age of 96. Many other icons of the craft have paid tribute to the crooner in the days since his passing and now we are paying our respects in our own way. The following is a look back at some of the moments when Bennett tried his hand at acting and, in particular, as the greatest role he ever played: himself.
The Scout (1994)
One of Bennett’s earlier cameos as himself is in two scenes from one the earlier films of Academy Award winner Brendan Fraser’s career and one of the most underrated, great sports movies of the ‘90s, as well, The Scout. Bennett first appears at his own concert, where he points out that the latest New York Yankee — Fraser’s character, Steve Nebraska — is in the audience, before the young baseball pitcher precedes to upstage the crooner with his rendition of “I Left My Heart in San Francisco,” much to the embarrassment of the man who recruited him, Al Percolo (Albert Brooks). He shows up again to sing the National Anthem for Game 1 of the World Series, where Nebraska is playing.
Analyze This (1999)
Another time in the ‘90s when Bennett performed a classic tune in a movie was in the final scene from Analyze This. One of the best movies co-written and directed by the late Harold Ramis — who also had some notable, if not underrated, movie appearances of his own — this comedy is about a psychiatrist (Billy Crystal) who is reluctantly assigned to treat a mafia criminal (Academy Award winner Robert De Niro) reeling from a near-death experience. Bennett is seen performing “I’ve Got the World on a String” during a personal show for Crystal’s character, Ben Sobel, following his marriage to his new wife, Laura (Lisa Kudrow).
Bruce Almighty (2003)
Another great comedy starring a Friends cast member in which Bennett makes a brief, but quite memorable appearance is one of the best Jim Carrey movies, Bruce Almighty. This time, he is performing at a restaurant where our title character (Carrey) is having a celebratory dinner with his girlfriend, Grace (Jennifer Aniston), who is shocked when Bruce exchanges casual glances with the singer. What really perfects the scene, however, is that Bennett is singing “If I Ruled the World” in a movie about a man who gets the chance to do just that when he is imbued with the power of God (Morgan Freeman).
Entourage (2008)
Bennett would also make cameos on a number of TV shows, such as on the long-running, Emmy-winning dramedy, Entourage. In the Season 5 episode, “Unlike a Virgin,” Vince (Adrian Grenier) has a run-in with his singer ex-girlfriend, Justine, (Gossip Girl cast member Leighton Meester) who invites him and his friends to watch the making of her latest music video, which also features Bennett. Justine introduces Vince to Bennett, who happens to have been a big fan of his performance in James Cameron’s Aquaman movie, and expresses his regret of not seeing the sequel, to which Vince assures him it is find because Jake Gyllenhaal assumed the role for that one.
Saturday Night Live (2006)
After years of being impersonated on SNL by Alec Baldwin as the host of his own talk show, The Tony Bennett Show, Bennett appeared alongside the Saturday Night Live host hall-of-famer in one of the last editions of the sketch, but not as himself demanding retribution for mockery like some others have. The singer -- going by his actual legal name, Anthony Benedetto -- seems to appear in the bit as a thank you for Baldwin’s sincere approach to imitating him by playing a nearly starstruck Tony Bennett impersonator who reveals he performs the singer's biggest hit under the stage name, “Phony Bennett.”
30 Rock (2012)
Years after his SNL cameo alongside Baldwin, Bennett appeared on a show poking fun at what goes on behind the scenes of a sketch comedy series that also starred Baldwin, 30 Rock, in Episode 7 of Season 7, “Mazel Tov, Dummies!” In it, Liz Lemon (creator Tina Fey) is having a courthouse wedding to Criss (James Marsden) which — keeping in tone with any of the best 30 Rock episodes — is chock-full of absurdities, among them the sight of a singing Bennett.
Muppets Most Wanted (2014)
Another time when Bennett appeared in a title also starring Tina Fey was in 2014 with an appearance in Muppets Most Wanted (one of the movie’s many great celebrity cameos) for a scene that parodies Hollywood’s obsession with sequels. The meta moment sees Bennett working the craft services table on the set of the movie with his frequent collaborator, Lady Gaga (who also shared a lasting friendship with Bennett, as Rolling Stone recalls).
Blue Bloods (2011)
Lady Gaga is just one of many modern talents whom Bennett would perform duets with some of the most revered musical talents working today, such as Lady Gaga Carrie Underwood. The American Idol winner was seen performing a beautiful rendition of “It Had to Be You” with Bennett on the Season 2 premiere of the CBS crime drama, Blue Bloods, at a fundraiser attended by Frank Regan (Tom Selleck) and his daughter, Erin (Bridget Moynahan).
The Simpsons (1990)
Many of the best episodes of The Simpsons are known for their celebrity cameos, but the first person to ever lend their voice to the series as themselves was none other than Tony Bennett. It was in the Season 2 episode “Dancin’ Homer” when he appeared to sing a song called “Capital City” — a parody of “New York, New York” — while running into the titular family as the tour the eponymous urban community.
Bennett was a one-of-kind talent whose presence warmed your heart no matter what he was doing. The nine appearances on the big and small screen above are just a handful of examples to prove that.
