30. Ice Cube - "My Summer Vacation" (1991)
From the incendiary Death Certificate LP, "My Summer Vacation" is a morality tale wrapped in Compton gang colors. Tired of police harassment and rival gangs, Ice Cube and his Lench Mob move their drug-dealing business to St. Louis. They fly into town, take over a local drug spot by way of a drive-by shooting, and set up shop. It all seems easy enough at first: The money rolls in, and there doesn't seem to be much competition. Very quickly, however, everything goes awry. The local dealers retaliate, leaving Cube's friend dead. Cube himself ends up in jail facing a life sentence. It's a gripping track, and apparently based on a true story. -MA
29. The Blind Eyes - "Hold Down the Fort" (2011)
Brick thieves are a particularly odious scourge of the city's north Ssde, pilfering the literal building blocks of homes caught between disrepair and demolition. Sure, copper thieves are a bunch of bastards, too, but those red bricks are the central hue to the literal landscape of St. Louis (watch local filmmaker Bill Streeter's Brick By Chance or Fortune for proof). So the Blind Eyes' singer and guitarist Seth Porter isn't being metaphorical in the opening gambit to this standout from With a Bang, but he also looks at these wandering bricks as a symbol of a city that's been chipped away at piecemeal, both in its historic infrastructure and in dwindling population numbers. With an economical tightness reminiscent of the Jam or Ted Leo, the band motors through the verses before launching into a spirited coda that neatly sums up much of St. Louis' inferiority complex: "The cure to all your ills is heading for the hills," sings Porter. He's right, of course -- many native sons and daughters light out for the coast, but just as many stay and put their backs into the work of maintaining and rebuilding what we have. -CS
28. Jeanne Trevor and Ray Kennedy - "Spring Can Really Hang You Up the Most" (2000)
The story of "Spring Can Really Hang You Up the Most" is a thumbnail sketch of the Central West End's cultural legacy. The New York-born lyricist Fran Landesman moved to St. Louis with her husband Jay, and together they ran the Crystal Palace nightclub in Gaslight Square. Together, the Landesmans wrote a play called The Nervous Set, inspired in part by the fertile, beatnik-esque arts scene of their club. The musical went nowhere but this central ballad endured as a jazz standard, which reinterprets one-time CWE denizen T.S. Eliot's opening salvo from "The Waste Land." That poem's "April is the cruelest month" was recast as beatnik slang for the song's title, but along with pianist Tommy Wolf's languorous musical composition, the song transmits the ennui that comes with changing seasons and stagnant lives. Many of the big voices have taken a swing at this one -- Sarah Vaughan, Ella Fitzgerald, Barbra Streisand (herself a former Crystal Palace performer) -- but it's our own town's Jeanne Trevor who connects the song back to its roots. Her version comes from Ray Kennedy's The Sound of St. Louis album, in which the local pianist interprets the best songs of St. Louis -- most of which appear somewhere on this list. -CS
27. World Saxophone Quartet - "Hattie Wall" (1987)
East St. Louis, including the satellite town of Brooklyn, Illinois, was a crucible of American music. Gospel, blues and jazz flourished in the clubs, churches and social gatherings of the city, and musicians like Miles Davis, Ike Turner and Chuck Berry soaked it all in and gave back to it. So too did composer and baritone saxophonist Hamiet Bluiett, one of the driving forces of the pioneering World Saxophone Quartet. The original lineup of the group featured Bluiett, David Murray, Julius Hemphill and Oliver Lake, and it's that quartet you hear on the theme song "Hattie Wall," a tribute to Bluiett's aunt, who ran the popular Harlem Club in Brooklyn. If you're seeking the roots of jazz-funk, search no more. -RK
26. Uncle Tupelo - "New Madrid" (1993)
Hard not to feel nostalgic about this track, harder still not to sing along. "Come on do what you did / Roll me under New Madrid," harmonize Jeff Tweedy and Jay Farrar, because in 1993 they were still singing together, still drawing on each other for inspiration. "Shake my baby and please bring her back" -- back to Belleville, Illinois, the band's home. "New Madrid," like much of the band's place-minded catalog, neatly and unpretentiously captures what it means to still be from that town across the river: the opening banjo plucks, the daydreams that turn into disasters, the skepticism about the big city. In the song, the Mississippi burns and runs backward, as it was fabled to have done during the mighty New Madrid quake of 1811-'12. That fault line, some locals believe, runs straight beneath the Belleville fountain, where Tweedy wishes he could walk again with his girl. Three years before the song was written, climatologist Iben Browning had predicted the world as Jeff and Jay knew it would end courtesy of that notorious Midwestern fracture. In the context of Uncle Tupelo's story, the line "buries us all in its broken back" now sounds like a very different kind of presage. -RK
25. Judy Garland - "Meet Me In St. Louis, Louis" (1944)
Let's all sing it together, shall we? Few St. Louis songs are as revered as this one, and while you'd be hard-pressed to find anyone who can recite the oddball verses, the chorus paints our town and its World Fair as the center of the known universe. Written by Tin Pan Alley composers Andrew B. Sterling and Kerry Mills in 1904, the song was reborn 40 years later in the MGM musical of the (nearly) same name, and Judy Garland's performance gave a whiff of turn-of-the-century optimism for post-war Americans. You can tell us the lights are shining any place but here, but we won't believe you. A good St. Louis song has a special glow. -RK
24. Sleepy Kitty - "Hold Yr Ground" (2014)
Paige Brubeck kicks off the final track to Sleepy Kitty's second album as an open letter: "To whoever stole the Dodge Caravan on June 11, 2010..." But rather than spew vitriol at thieves, she turns the song into a rumination on life in the city, both for the supposed teenager who ran off with her wheels and for herself. The song addresses the highs and lows of city living, recognizing that the crime and poverty that plagued the band's beloved Cherokee Street has given way to progress. But that progress only comes from keeping your feet planted. "Hold Yr Ground" celebrates those who haven't abandoned St. Louis' urban grit for more verdant pastures. -CS
23. Henry Townsend - "Cairo Is My Baby's Home" (1962)
Though born in Shelby, Mississippi, in 1909 and raised in Cairo, Illinois (150 miles south of St. Louis), Henry Townsend embodies a rural thread of the blues that's well worn in the mythology yet often lost in discussions of St. Louis music. Originally "Cairo Blues" belonged to the awesome (and under-recorded) Henry Spaulding. It later became a signature for Townsend, even kicking off his classic 1962 album for the Bluesville label. Backed on that recording by his St. Louis protégé Tommy Bankhead, Townsend navigates the challenging rhythms with deceptive nonchalance, even as he tells of the Cairo women who will treat you "kind and sweet" one minute and then slash you the next. -RK
22. Thee Dirty South - "Top of the Dirty South" (2007)
Bob Reuter didn't live long enough to see this list, and he would have bristled at the choice. But he bristled at everything, and there are so many of his fiery, poignant songs of St. Louis to choose from. Written during his transition from the Americana Kamikaze Cowboy to the punk-bluesy Alley Ghost, "Top of the Dirty South" howls with despair and pride. As guitarist Marc Chechik slashes, the lifelong St. Louisan snarls: "These red bricks were made to hold the heat/I got this fan in the window sucks it in off the streets...I got nothin'!" It was a lie -- he had this and a hundred more great songs -- but it cut like the truth. -RK
21. Grant Green - "The Holy Barbarian Blues" (1959)
An integrated beatnik hangout and jazz club in the DeBaliviere neighborhood in the late '50s didn't really stand a chance. The Holy Barbarian, located at 572 DeBaliviere Avenue, made history when it hosted an up-and-coming guitarist named Grant Green playing with organist Sam Lazar, drummer Chauncey Williams, and sax man Bob Graf. The club was newly opened, so maybe Green had something to prove; maybe he was just burned out on the strip-club gigs. This tune is Grant at his hard-bopping, single-note-speeding best. With sinew, precision and a million twanging notes, he blows the berets off the room. It was Christmas 1959, the club would close in the new year, and Green would head to New York for a stunning career with Blue Note Records. He never again recorded in St. Louis. He didn't have to. -RK
