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Whether he wanted this status or not, it's true that Berry was the first rock n' roll outlaw, and one of rock's first big stars. "Sweet Little Sixteen," a song dedicated to fan culture and teenage dreams, is an ode to the idea of fame itself. It evokes images of bandstands and screaming girls, the stuff of the movie Hairspray and part of our current caricature of the 1950s. But after his time in prison and the decline of his status as a superstar, Berry's approach to fame became more and more eccentric over the years. By the 1970s, he was somewhat infamous for giving terrible live shows. He never traveled with a band, choosing to play with random pick-up bands in each new city he traveled to.
Bruce Springsteen and the E Street Band randomly backed up Chuck Berry during that period, and the story he tells about it is pretty amazing. According to the Boss (who was not uber-famous just yet), he and the band nervously awaited Berry at a club. They waited and waited, and Chuck just didn't show up. The opening act went on, and still no sign of Berry (keep in mind that Springsteen had never met nor played with Berry, so this was a nerve-wracking situation at a minimum). About five minutes before the Berry set was supposed to start, he arrived in no particular hurry—alone, driving his own Cadillac and carrying nothing but a guitar case. The band rushed to meet him and try to get in a little rehearsal, but Berry bee-lined for the booking agent and disappeared into a backroom where he was apparently paid in cash (as he was for every show, even when he was getting paid tens of thousands of dollars). After getting his money, Berry cruised out to the backstage area, tuned his guitar, and met the band.
According to Springsteen, he and the band desperately tried to find out what they'd be playing, and what key they'd be playing in. Berry just said, "We'll be playing Chuck Berry songs." They rushed on stage and stumbled through a set, with Berry periodically turning to the band and saying "play for the money, boys!" Ironically, Springsteen and the E Street Band weren't getting paid. As he tells it, playing with Chuck Berry was one of the most terrifying performance experiences of his life.
So, that's Chuck Berry. Apparently all that generous payment in cash came back to haunt him, and he actually went back to prison for a few years in the late 1970s for tax evasion. But he was undeterred: though he did study accounting while in prison and start paying taxes, he still tours with nothing but a suitcase and a guitar, refusing to travel with an entourage and insisting on cash payment before his performances. We've already called him a penny-pincher a couple times, but that might be an understatement. Berry's approach to being a star could even be considered strangely stingy. No one really follows the Berry psychology, but it's a part of his calling card at this point to be an enigmatic star, protective of his expansive wealth and perhaps unaware of his own brilliance.
Chuck Berry's writing is poetry, plain and simple. He was one of the earliest rockers to write his own songs—an example of a singer-songwriter before the days of Dylan—and from "Maybelline" to "Sweet Little Sixteen," his songs resonated with teen audiences and made a point with older crowds at the same time.
"As long as the music has something to do with your walk of life, I think that people will listen. So that's why I wrote about schools…and I wrote about cars…and I wrote about love," said Berry. The point here is that he was able to write about whatever topic he chose, not limited to personal experience or rote heartbreak themes.
Berry's song writing skills didn't come easy. While he was finishing up his high school diploma in prison, he studied poetry on his own volition, learning a wide array of poems by heart. "Poetry is my bloodflow," he has said—and friends and interviewers attest that he can still recite Longfellow and Whitman decades later.
One of the notable ways that poetry influenced Chuck Berry's songwriting in "Sweet Little Sixteen" is his use of geographic locations. This trope—listing off places cross-country road-trip style—is very American, dating back at least to the geographically oriented poetry of poets like Walt Whitman. Cities are a lasting theme in lots of modern poetry, and it could be argued that Whitman made writing about city and state names into a sort of American poetry tradition. He was followed by everyone from Chuck Berry to Beat poet Allen Ginsberg, who honored the eclectic nature of American culture and geography in his controversial works. Other American authors whose works explore the idea of cross-country travel include John Steinbeck, who wrote about Oklahoma families traveling West during the Great Depression in The Grapes of Wrath, and Mark Twain, whose Adventures of Huckleberry Finn uses a series of voyages through the American South to talk about slavery and social issues.
Berry's songwriting is a bit less risk-taking than Walt Whitman or Allen Ginsberg (and a bit less literary than Steinbeck or Twain), but it exists in the same spirit: celebrating the wilder side of U.S. culture and reveling in the broad geographic span of the country.