Tony Bennett Was The First Celebrity To Appear As Himself On The Simpsons
When "The Simpsons" debuted on December 17, 1989, it was an instant sensation. Matt Groening's bizarre, weirdly proportioned yellow people felt like a dark antidote to the corny TV Americana that had persisted through Reagan's America, and the show's popularity proved that audiences were ready for a change. Plus, it was incredibly novel to have an animated sitcom in primetime, leading many curious souls to tune in ... and instantly become hooked. Many years later, celebrities would be fighting tooth-and-nail to gain a coveted guest spot on "The Simpsons," either playing themselves or playing a character.
A fun piece of trivia: the first celebrity to guest-star in an episode of "The Simpsons" was Albert Brooks (no relation to show producer James L.). Albert Brooks played a character named Cowboy Bob in the 1990 episode "The Call of the Simpsons." Cowboy Bob was very eager to sell an RV to the status-seeking Simpson family. Recall that in the show's early episodes, Homer (Dan Castellaneta) was obsessed with achieving suburban normalcy with his off-kilter family. This was long before he was transformed into a cretin. Homer longed to buy an RV to show up his wealthy neighbor. Cowboy Bob was the one who realized that Homer had terrible credit, and could only afford the worst RV on the lot. Brooks also played Jacques in "Life in the Fast Lane," and Penny Marshall showed up as Ms. Botz in "Some Enchanted Evening," both from that same year.
The first "Simpsons" celebrity guest voice to play themselves, however, was the late, great Tony Bennet, who sang a number and introduced himself in the second season episode "Dancin' Homer." Less than a year into its life, and "The Simpsons" already featured one of the world's great crooners.
Capital City!
In "Dancin' Homer," the alcoholic Simpson patriarch is at his local dive bar lamenting his sorry life state. The barflies around him correctly assume that Homer is especially sad because he once brushed against greatness. This was the case. Homer tells a story of how he once went to a local baseball game and, in a fit of pique, began dancing for the crowd. He worked the crowd into a frenzy of excitement and the local team won the game as a result. Homer was then hired as the team's regular mascot. His shenanigans captured the attention of the closest Major League Baseball team, the Capital City Capitals. Famously, "The Simpsons" has always been coy about its geography, so Capital City is in whatever state you might want.
When the Simpsons drive into Captial City to pursue Homer's new job, they are all dazzled by the bright lights of the sophisticated urban center. They ogle landmarks that are alien to the audience, but clearly a big deal for the Simpsons (The Penny Loafer restaurant! 4th Street and D!). As they drive, Tony Bennett sings about Capital City on the soundtrack. The tune is meant to be reminiscent of "New York, New York," but mildly comedic. "It's the kind of place that makes a bum feel like a king, and makes a king feel like a nutty, cuckoo super king."
Then, what a surprise! The Simpsons' car pulls up next to Tony Bennett himself! Marge (Julie Kavner) recognizes him. He wears a suit and holds a microphone. "Hey, good to see you!" he says. Tony then goes back to singing about Capital City.
Before you 'Well, actually' me...
There was, of course, one other notable celebrity to have appeared on "The Simpsons" after Brooks and Marshall but prior to Tony Bennett, but don't try to get me on a technicality. In the very first "Treehouse of Horror" Halloween special (which aired on October 25, 1990), one of the segments was a truncated dramatization of Edgar Allan Poe's famous poem "The Raven." Homer imagined himself as the protagonist of the poem, and his son Bart (Nancy Cartwright) as the titular avian. Poe's actual poetry was read menacingly by James Earl Jones. Jones also played a moving truck driver in the show's first segment, and a drooling space alien named Serak the Preparer in the second ("This will give the humans the perfect flavor!").
One might want to make the argument that Jones was the first celebrity to play himself on "The Simpsons," but I want to stop you right there. For one, Jones never introduced himself in "The Raven," nor did an animated version of the actor appear onscreen. He was merely a narrator and was even credited as such. One might even argue that he was playing Poe himself. Regardless, he was not playing James Earl Jones.
Bennett, meanwhile, would appear in a 2002 episode of "The Simpsons" called "Bart vs. Lisa vs. the Third Grade," only he did not return to the recording booth for his appearance. It was, instead, constructed from archived audio. His "Capital City" song would also appear in the 2013 episode "Whiskey Business."