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Like so many of his peers, Sain grew up in and around the Delta region of rural Mississippi. As a teenager, he served as drummer in a band with his stepfather, famed Delta blues pianist Willie Love. The band also featured the legendary Sonny Boy Williamson on harmonica and vocals. Today, Sain looks back on his stepfather's music with respect and admiration. At the time, however, he was less enthusiastic. "Willie had some great songs, and they're great to me now more than they were then," he says. "Because I was young then and he was my stepdaddy, I didn't pay that much attention to him. But today, man, that stuff is awesome."
Sain also worked with the likes of Howlin' Wolf, but it was his experiences with musicians his own age that most excited him. By the late '40s, he'd formed his own band with vocalist Little Junior Parker and guitarist Matt "Guitar" Murphy. Sain recruited the latter from Howlin' Wolf's band. The notoriously feisty Wolf was not amused. "He stayed mad at me for a long time after that," Sain recalls with a laugh. "It's funny now. It wasn't quite as funny then."
By the early '50s, Sain was living with his mother and stepfather in Greenville, Mississippi. It was there that Sain met singer and guitarist Little Milton. It also was there that he first picked up a saxophone. Soon he was back to working with Love, Williamson and Wolf -- but this time as a horn player.
By the mid-1950s, Sain found himself in Chicago, where he again hooked up with Howlin' Wolf and, eventually, the great Elmore James. Chicago offered plenty of work for Sain, and his connection with Wolf led to some national tours, including one that culminated at the Apollo in Harlem. But Chicago didn't captivate Sain in the way that it had so many other blues musicians. "It was cool, but it wasn't my favorite place," he says, "so when I got the opportunity to get the hell out of there, I did."
The opportunity finally arrived in 1959. "When I came to St. Louis, I planned to stay a weekend," Sain admits, "but I've been here for more than 40 years." The impetus for his trip to the city was a gig with longtime pal Little Milton Campbell. Sain was shocked by St. Louis' raucous nightlife. As a boy, he'd lived for a period in St. Louis and hadn't enjoyed the experience. "Oh, I hated this place then," he says with a laugh. "It was gloomy and dark and smoky. I was from the South. I was used to bright sunshine and warmth."
As a young man, Sain's priorities were different. He saw in St. Louis opportunity -- and plenty of it. "St. Louis was jumping then, man," Sain says. "Little Milton, Ike Turner and a couple of other people had changed the scene here." Social clubs and big bands were out; hard-driving R&B outfits were in. Sain's weekend gig stretched into two weekends, then a month. Almost immediately he took on the role of bandleader for Campbell's group, one of the hottest groups in a city filled with legendary acts such as Ike Turner, Albert King and Chuck Berry.
The appeal of Little Milton's band, says Sain, was its members' ability to keep up with current musical trends. "The other guys who were here already and played guitar, played the blues, they would only do old stuff," Sain explains. "But Milton came in doing stuff off the radio. We were like a jukebox band, and we played whatever was popular."
Campbell and Sain, however, were not content merely to ape the music of other groups. Soon they were writing their own material. Sain's first songwriting effort, "Same Old Blues," was recorded by Campbell and released on the locally owned Bobbin Records label in 1959. The song didn't do much, but it wasn't long before Sain and Campbell started seeing chart success.
In early 1962, "So Mean to Me," a song co-written by Sain, stormed up the R&B charts to the lofty position of number fourteen. But it wasn't until 1965 that Sain penned what is probably his greatest contribution to the lexicon of R&B music: "Don't Mess Up a Good Thing" was recorded as a duet by St. Louisans Fontella Bass and Bobby McClure. The song was a massive hit, and Sain has been reaping the benefits ever since.