10. Wilco - "Casino Queen" (1995)
In the wake of the 1993 flood, some members of the flock thought that the mighty rain was God's retribution for those sinful riverboat casinos. Jeff Tweedy gives some credence to that idea on this parodic take on the gambler's blues. As Brian Henneman's guitar nails a blues-charged, Stonesy riff and Max Johnston saws away on fiddle, the protagonist prowls the decks of the Casino Queen, that neon-and-flashbulb showboat perennially docked on the east bank of the Mississippi, and finds nothing but bad luck and sketchy romantic prospects. Wilco's fortunes would only improve, and this tribute to Tweedy's side of the river showed that the band could graft pop hooks onto the alt-country template that its predecessor band, Uncle Tupelo, forged. -CS
9. Scott Joplin - "The Entertainer" (1902)
Scott Joplin didn't invent ragtime, but his songs perfected and typified the form. He came to prominence during his time living in Sedalia with the success of 1899's "Maple Leaf Rag," but his move to St. Louis in 1901 led to more acclaim (and a profitable relationship with local music publisher John Stark). Joplin was living and performing in St. Louis when he wrote "The Entertainer," and few songs feel as elementally American as Joplin's composition. The song's syncopation and evolving melody would later morph into jazz, and strains of "The Entertainer" are still heard ringing out from ice-cream trucks and emanating from grade-school piano recitals to this day. -CS
8. Chingy - "Holidae In" (2003)
"Right Thurr" introduced Chingy as St. Louis' best shot at a post-Nelly superstar, but this slice of hotel hedonism endures. It doesn't hurt that the Trak Starz team drops some ridiculously punchy, jiggly beats, or that Chingy's label boss Ludacris drops a chorus and Snoop Dogg bookends the joint in his inimitable style. It is unclear if the actual Holiday Inn St. Louis-Airport (not far from his stated location at I-270 and Natural Bridge Road) truly offers valet service, but in Chingy's world, "Holidae In" is a state of mind reachable with enough VSOP and sticky-icky. -CS
7. The Skeletons - "St. Louis" (1992)
"Show me the way to St. Looouuisss, show me!" Talk about irresistible choruses. Like "St. Louis Blues," the song "St. Louis," originally by Aussie rockers the Easybeats (of "Friday on My Mind" fame) is an archetypal anthem of the river city, written by those who never called it home. Though the Easybeats' 1968 original is fantastic, and covers by British rockers Warhorse and Albert Lee have their charms, it's Springfield, Missouri band the Skeletons, flexing all its Midwestern rock & roll and R&B muscle, who best capture the spirit of a song that should be blasted out at stadiums all over this land. -RK
6. Duke Ellington and His Washingtonians - "East St. Louis Toodle-Oo" (1927)
Duke Ellington's first charting single paid tribute to that toddling town just across the Mississippi River, and its minor-key take on Dixieland jazz paints the titular city in shades of deep blue and percolating red. The rhythm, for Ellington, was like "the broken walk of a man who had worked all day in the sun and was leaving the field at sunset." Co-writer Bubber Miley left an indelible imprint on the song (and on trumpet technique) by employing a plunger-mute on his horn, giving the melody a rasping, slurring style. The tune was Duke's theme song for years; Steely Dan gave it an update on 1974's Pretzel Logic. -CS
5. Chuck Berry - "Back in the U.S.A." (1959)
What does Chuck Berry mean to America? Everything. What does America mean to Chuck Berry? Pretty much the same, but with an extra helping of money upfront and St. Louis right behind. For Berry, to be "Back in the U.S.A." meant to be back at his home "in ol' St. Lou," to have the freedom to be a rock & roller. It also meant a creative common ground with his partner, Johnnie Johnson, who deserves so much credit for the freewheeling sound of Berry's national anthem. "Uh huh, oh yeah!" go the backup singers, thump go the drums, and up-and-down and inside-out go the keys of Johnson, as driving as boogie-woogie, as virtuoso as bebop, as American and as St. Louis as all get-out. -RK
4. Lloyd Price - "Stagger Lee" (1959)
As tall tales go, St. Louis has no greater myth than the story of how "Stack" Lee Shelton murdered Billy Lyons on Christmas night, 1895. The song's purported title has as many variants ("Stagolee," "Stackerlee") as there are cover versions. Everyone from Fred Waring's Pennsylvanians to Mississippi John Hurt to Ike & Tina to the Clash have performed the song, but Lloyd Price's thrilling 1959 single topped both the R&B and pop charts, but not before an alternative version was censored by none other than Dick Clark. The media mogul should have saved his breath. The story of Stagger Lee -- that elusive, vengeful man -- has proved unstoppable. -CS
3. Nelly - "Country Grammar (Hot Shit)" (2000)
Nelly didn't just give St. Louis its first hip-hop superstar with the release of Country Grammar; he also gave our citizens a bona fide motto with its title track: "Sing it loud -- I'm from the Lou, and I'm proud." In the early 2000s, that phrase might as well have been suspended from the Arch. The song's nursery-rhyme chorus belies its streetwise swagger -- his street sweeper doesn't come from the department of sanitation. Reaching No. 7 on the charts, "Country Grammar" placed Nelly and St. Louis hip-hop on the national map. -CS
2. Oliver Sain - "St. Louis Breakdown" (1972)
Look and listen closely: Oliver Sain is everywhere, not just in this list, but in the music of St. Louis: past, present and future. Producer, songwriter, arranger, impresario, multi-instrumentalist -- he did it all, from hot R&B to free jazz, from conscious soul to dirty funk. "St. Louis Breakdown," stutter-strutting and greasy as a barbecue baster, is Sain's calling card. "I want everybody to get up and do the St. Louis Breakdown!" And he means everybody, shouting out to the babes in hot pants, the hippies in San Francisco, his funk brother Rufus Thomas in Memphis. Sain let the world know where it's at. -RK
1. Bessie Smith and Louis Armstrong - "The St. Louis Blues" (1925)
Imagine a world without "The St. Louis Blues." And after you've emerged from your despair, remind yourself of just how amazing this song is. Savor every image, every note -- especially as performed by Bessie and Louis. Published by W.C. Handy in 1914, the song is the cornerstone of American music. Remove it, and the palace collapses. Handy claimed that he first heard the blues on the levees of St. Louis. This line from the song, "My man's got a heart like a rock cast in the sea," also traces back to this river town. When Bessie sings the tune, she slows down time and stretches her lines, while Louis improvises as if to lift her spirit. After all the versions, as numerous as the rocks in the sea, Bessie and Louis' 1925 recording reigns supreme: luminous, mournful and intoxicating as that evening sun going down -- in St. Louis and around the world. -RK
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