Taylor Swift, Huey Lewis, Randy Newman, and More

When Bob Dylan played Nautica on the Cleveland waterfront in the summer of 1991, he broke out a cover of “Pancho and Lefty” by Townes Van Zandt. “That’s about the only song in my repertoire that’s got Cleveland in it,” he said. “Is there a president by that name too?” Unlike most of the songs on this list, “Pancho and Lefty” isn’t predominantly about Cleveland (which is why it isn’t ranked much higher), but it is where poor Lefty finds himself at the end of this sad tale about a couple of doomed outlaws. “Lefty’s living in a cheap hotel,” Van Zandt sings. “The desert’s quiet, Cleveland’s cold/So the story ends, we’re told.” (He never specifies which “cheap hotel” Lefty picked, but whenever I drive past the dreary Solon Motel on Aurora Road, I picture Lefty hunkered down in one of the dingy rooms.)

Original Stone Temple Pilots frontman Scott Weiland spent a decent chunk of his childhood in Cleveland. On “Missing Cleveland,” the leadoff single from his 2008 solo LP, “Happy” in Galoshes, Weiland looks back at that chapter of his life with no small amount of regret and nostalgia. “You’re holding on but letting go,” he sings. “I’m missing Cleveland and the snow/And lonely bars where everybody knows.” Much like Townes Van Zandt, Weiland focuses on Cleveland’s shitty weather in the winter. But it should be noted that Cleveland is quite warm in the summertime and is beautiful in the fall and spring. There’s also a certain majesty to a Cleveland winter only appreciated by true locals.

On Kid Cudi’s debut mixtape in 2008, A Kid Named Cudi, the rapper born Scott Ramon Seguro Mescudi told his fans about the city where he grew up. “Ain’t no city like Cleveland,” he raps. “Cruisin’ with my bad bitch in the evening/You wanna know exactly why I’m this way?/Take a trip to the land, swing this way…Cleveland is the reason I’m cool.” Unlike other songs on this list, this is a proud, unapologetic, even boastful song about the city. He released it before most people had heard of him, and he’s gone on to much bigger things, but he’s never turned his back on his hometown and remains the pride of Solon.

At first glance, R.E.M.’s 1986 classic “Cuyahoga” might seem like a tribute to Cuyahoga County or the Cuyahoga River, which runs through Cleveland and flows directly into Lake Erie. But it’s actually about the plight of Indigenous people in North America and their brutal treatment at the hands of the American government. “This land is the land of ours,” Michael Stipe sings. “This river runs red over it/We knee-skinned it you and me/We knee-skinned that river red.” Still, most Clevelanders simply hear the soaring chorus where Stipe sings the name of their county over and over. And R.E.M. rarely got through a concert in Cleveland or nearby Cuyahoga Falls without breaking it out.

Bone Thugs-N-Harmony put Cleveland on the hip-hop map with the release of their 1995 masterpiece E. 1999 Eternal, named after a street, specifically the 99th Street and St. Clair Avenue intersection, near where they all grew up. They’ve released many songs about the city over the years, but none expressed quite as much civic pride as 2002’s “Cleveland Is the City.” “Ya brotha wuz right here,” Bizzy Bone raps. “In the Columbus but they loved me not/When I went to Cleveland they said where you been/When I’m unconditional with my loving.” The group is currently on the road with Wu-Tang Clan, though there’s much internal rancor since Layzie Bone wasn’t invited to take part, and Bizzy Bone has also been on the outs many times over the years. But even though it’s hard to get all five of them on the same page about much of anything these days, the one thing they agree on is that “Cleveland Is the City” forever and ever.

Most U.S. cities have at least one Michael Stanley. He’s the local rock star who was once right on the cusp of national success, but it never quite happened. But instead of moving to New York or L.A., they remain where they are and become hometown heroes, even if it means taking a day job to pay the rent. (In Pittsburgh, this is Joe Grushecky.) The Michael Stanley Band had a moment in the early 1980s where it seemed like they might become the next Bruce Springsteen and the E Street Band, and they even sold out four consecutive nights at Blossom Music Center in August 1982. But despite the minor hits “He Can’t Love You” and “In the Heartland,” they never really found a following outside of Northeast Ohio. The band split in 1987, and Stanley spent decades as one of the main disc jockeys on Cleveland’s classic rock radio station WNCX before dying from lung cancer in 2021. But his music lives on with his 1983 Cleveland ode “My Town,” which is a staple of the Ohio State Marching Band and one of the unofficial anthems of Cleveland.

Huey Lewis had such a great time during an early 1980s gig in Cleveland — which has been an enormous market for rock concerts going back to the 1950s — that he began writing a song titled “The Heart of Rock and Roll” with a repeated refrain of “The heart of rock and roll is in Cleveland.” And had he stuck with that, this song would likely be at the top of our list. But not wanting to shortchange other markets, he changed it to “the heart of rock and roll is still beating” and ran through a long list of other cities. Still, at the very end of the song, during a climactic moment, he revealed his true thought by bellowing, “In Cleveland!” To Clevelanders, those two words are the actual heart of the song.

There are great songs throughout rock history like Queen’s “Bohemian Rhapsody” or the Beach Boys’ “Surf’s Up” that require rigorous lyrical analysis to understand their true meaning. And then there’s Ian Hunter’s 1979 anthem “Cleveland Rocks,” which is about the city of Cleveland rocking. Like others on this list, Hunter toured all over the world and saw something special with Cleveland audiences. (It’s no surprise Cleveland is where Elvis Presley first performed north of the Mason-Dixon line or where David Bowie unveiled Ziggy Stardust to an American audience.) “Cleveland Rocks” had a second life in 1997 when the Presidents of the United States of America recorded a version that became the theme song for The Drew Carey Show.

Technically, this 1969 classic is most likely about the small town of Cleveland, Texas. Robbie Robertson wrote it during the height of the anti-Vietnam protests (referred to here as “the storm”) that were sweeping America. “Look out, Cleveland, the storm is comin’ through,” Robertson wrote. “And it’s runnin’ right up on you/Look out, Houston, there’ll be thunder on the hill.” The giveaway is that Houston is just 45 miles from Cleveland, Texas. That said, Robertson never outright said the Cleveland of the song is Texas. And so many people have embraced it as an Ohio song, and it’s such an incredible work, that we have to include it here. To the good people of Cleveland, Texas, all 9,936 of you, our apologies.

Cleveland was not in a good place when Randy Newman recorded “Burn On” for his 1972 LP Sail Away. The Cuyahoga River was so polluted that it burst into flames in 1969, sparking humiliating headlines all across the country. The factories that built the city were closing, the population was sinking, the crime rate was rising, and more and more people were referring to it as “the mistake by the lake.” Newman didn’t hide from any of this in “Burn On,” and there’s certainly a bit of sarcasm in his words, but there’s also deep respect for the spirit of the town. “Cleveland, city of light, city of magic,” he sings. “Cleveland, city of light, you’re calling me/Cleveland, even now I can remember/’Cause the Cuyahoga River goes smoking through my dreams/Burn on, big river, burn on.” The song had a second life when it played over the opening credits of 1989’s Major League, during a period when the city was in even worse shape. (If we were ranking movies about Cleveland, Major League would also be at number one. It doesn’t even matter they filmed most of it in Milwaukee. It’s a Cleveland movie from beginning to end.)