Tony Bennett Had A Storied TV And Film Career – Usually Playing Himself

Tony Bennett's first record, "Because of You" was released in 1952 and it instantly codified the entertainer as one of the music world's great crooners. In 1962, his 15th record, "I Left My Heart in San Francisco" was certified platinum by the RIAA, but that was after he had already established himself with Count Basie and his Orchestra and as a great fan of songwriter Harold Arlen. All told, he released 61 records in his decades-long career, not including his eight albums of collaborations and duets. He sang with Frank Sinatra, Barbra Streisand, Ray Charles, Carrie Underwood, Stevie Wonder, Natalie Cole, Mariah Carey, Bono, Sting, Paul McCartney, Diana Krall, and many others. Most recently, he released two collaborations with Lady Gaga in 2018 and 2021. Bennett passed away on July 21, 2023 at the age of 96. He will be deeply missed. 

Naturally, a talent of Bennett's stature couldn't be ignored by Hollywood, and he would appear on TV and movie screens periodically over the decades, usually playing himself. This author recalls discovering Bennett as a youth watching an early episode of "The Simpsons." When the title family visits the nearby Capital City, Bennet begins crooning to them on the soundtrack. He greets Marge personally. "It's the kind of place that makes a bum feel like a king," Bennett sang, "and it makes a king feel like some nutty cuckoo super king." Bennett was game to appear in anything, so long as he was permitted to sing. 

There was also at least one film in his career wherein he actually acted, and it has become strangely notorious for how misguided it was. Which, to my eyes, is a glorious benchmark that he could be proud of.

Bennett's first on-screen appearance came in 1959, with an appearance in a sixth-season episode of "The Danny Thomas Show." Technically, Bennett wasn't playing himself in that episode ... but he kind of was. The title of the show was "Tony Bennett Gets Danny's Help." Bennett played Danny Thomas' cousin Stephen, who dreams of breaking into show business. Thomas, an entertainer himself, takes Cousin Stephen to nightclubs where he can sing. Of course, Bennett sings multiple numbers. In 1963, Bennett returned to TV to play a small part in the comedic detective series "77 Sunset Strip." He played a character named Maximillian in the final two episodes of a five-part story arc about tracking a Nazi artifact across several countries.

It was in 1966 that Bennett tried his hand at acting for the first time, appearing in the turgid Hollywood melodrama "The Oscar." Directed by Russell Rouse (writer of "D.O.A." and "Pillow Talk"), "The Oscar" was about an ambitious Hollywood actor named Frankie Fane (Stephen Boyd) who, like in "All About Eve," treated people terribly and manipulated others merely to acquire his most desired bauble: an Oscar for Best Actor. Bennett played Frankie's nebbish friend Hymie, who occasionally feels like the film's narrator. There are scandals, childbirth deaths, and all manner of soap opera dynamics. It featured multiple Oscar winners and notable stars including Elke Sommer, Broderick Crawford, Milton Berle, Ernest Borgnine, Frank Sinatra, Hedda Hopper, and Edith Head (!). "The Oscar" was nominated for five Oscars and won zero.

"The Oscar" quickly became infamous for its hokey script and over-the-top performances. It was lambasted by critics, and is now only viewed as an oddity. Bennett's performance is earnest and he's devoted to the part, but his ease and naturalness stick out like a sore thumb in such an artificial movie. It was the last feature Harlan Ellison ever wrote, and it was the last time Bennett tried to "act."

After that, Bennett mostly stuck to TV to make cameos as himself. He performed on "The Doris Day Show" in 1970. He played himself in a few episodes of the 1978 miniseries "King," a biography of Martin Luther King, Jr. Paul Winfield played Dr. King.

For the most part, Bennett would appear in movies and on TV as a smiling angel, flitting in to give a blessing to the production and sing inspiration into the characters. He appeared on "Evening Shade" in 1994 playing a very Tony Bennett-like character named Tony Lombardi. That same year, he appeared in Michael Richie's comedy film "The Scout" as himself. By the late 1990s, with his decades-long celebrity as an old-school lounge singer firmly cemented, he started appearing on TV more and more, largely to elicit cheers of recognition and excitement from the audience. He showed up on "Suddenly Susan," on "Cybil," and on the '90s Bill Cosby sitcom "Cosby."

In more recent years, Bennett blessed "Blue Bloods," "30 Rock," and "Entourage." Unsurprisingly, Bennett performed with the Muppets in "Muppets Most Wanted." His first appearance on "The Simpsons" was in 1990. He returned in 2002.

Bennett also appeared in a few additional studio films like "Bruce Almighty" and "Analyze This." In both, be played Tony Bennett.

For many younger people, Tony Bennett appeared on their radar when he was already in his 80s ... and still performing. Lady Gaga wanted to sing lounge standards with the legend, and the two appeared in a few slick music videos together. These were Bennett's final appearances on camera.

The final role Bennett acted in was on the Nickelodeon animated series "Wallykazam!," wherein he sang for a character named Bobgoblin in a 2014 episode. One can appreciate Bennett's gameness.

Looking over all his screen appearances, one can see one consistent feature: Bennett was always smiling. He was happy to be singing, even when he was belting out one of his more intense numbers. This may be another reason why "The Oscar" stands out; Bennett had to be dour for the first time. That stood in direct contrast to his stage persona, which was typically cheerful and welcoming. One gets the impression that Bennett loved his life and was happy to present music to the world. He never seemed bitter or spiky or overworked. He was an entertainer through and through.

Rest in peace, you glorious man. The world will miss you deeply. We are grateful for the hours and hours and hours of music you left for us to discover. With dozens of TV and film appearances and scads of records, we will be able to live with Bennett in perpetuity.