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Southern soul man Kip Anderson was born January 24, 1941 in Anderson, South Carolina — the son of a mother who taught music and a father who regularly played guitar at weekend fish-fry parties; from childhood forward he sang and played piano with his church gospel choir. At 13, Anderson was discovered by gospel legend Madame Edna Gallman Cooke, spending several summers playing in her touring group; he intended to follow her lead and pursue a career in spiritual music until he crossed paths with WOIC radio DJ and sometimes R&B singer Charles Derrick, who encouraged him to cross over to secular music instead. Anderson, Derrick, and friend Isaiah Hennie co-wrote the former's 1959 debut single "I Wanna Be the One," issued on the DJ's own Derrick label; when the single emerged as a regional hit, it was licensed for national distribution on Vee Jay but went nowhere, prompting Anderson to move to Savoy for the follow-up, "Oh My Linda," recorded with legendary session guitarist Mickey Baker. However, when the single's B-side, "Till Your Love Is Mine," appeared with Anderson credited as its sole songwriter, Hennie cried foul, and the dispute resulted in Savoy president Herman Lubinsky terminating the singer's contract.
Anderson landed at the Everlast label for his third single, 1962's "I Will Cry" — despite another superb performance, he earned little commercial notice and began supplementing his income by moonlighting in radio, first working alongside Derrick at WOIC before relocating to Fayetteville, North Carolina and settling in at WIDU. His next single, 1963's "Here I Am, Try Me," was recorded in Chicago at the famed Chess Studios but released on Anderson and Derrick's newly-formed Tomorrow label; 1964's "That's Why the Cryin' Begins" also premiered on Tomorrow but was subsequently licensed to ABC-Paramount, where it crept up to the number 79 spot on the Billboard pop charts. After two more Tomorrow releases, "I'll Get Along" and "Time Waits for No One," Anderson traveled to the legendary Muscle Shoals, Alabama-based Fame Studios to record "Woman, How Do You Make Me Love You Like I Do," the first of three singles issued on the Chess subsidiary Checker that together represent the creative apex of the singer's career — recorded in a gritty deep soul idiom perfectly complementing Anderson's powerful vocals; The follow-up "Without a Woman" was even better, and his third Checker release, "A Knife and a Fork," was better still, a witty, bluesy masterpiece later covered by the U.K. pub rock band Rockpile.
After his Checker contract expired, Anderson moved on to the Excello label, returning to the charts one last time with 1968's "You'll Lose a Good Thing," which cracked Billboard's R&B Top 40 chart; "Watch You Work It Out" soon followed, culminating with the devastating "I Went Off and Cried," arguably his best-known single. However, by 1970 Anderson was battling heroin addiction, forcing Excello to cut him loose — although he continued working in radio, his performing career dried up, and in 1977 he was sentenced to 10 years in Columbia, South Carolina's Central Correctional Institution. While serving his time he and several other inmates were allowed to form a gospel group, later appearing at local churches and community events under the watchful eye of prison guards; upon his release, Anderson returned to his recording career, cutting the gospel effort "I Coulda Been Sleeping" for the Lorma label in 1989. For Ichiban he delivered the 1992 full-length A Dog Don't Wear No Shoes, followed a year later by A Knife and a Fork — in 1996, he also collaborated with R&B singer Nappy Brown for the duet collection Best of Both Worlds, and for many years hosted a daily gospel show on Anderson radio station WANS AM.