Born in Indianapolis, Indiana in November 1908, Raymond Syd Valentine studied trumpet during the early '20s with Frank Clay, leader of the pit band at the local Washington Theatre. Valentine's first professional gigs took place during the mid-1920s with Fred Wisdom's Merrymakers in Kansas City, and in the company of clarinetist Jimmy O'Bryant with Paul Stewart's band in Terre Haute. After finishing high school, Valentine headed back to Indianapolis, where in 1927 he hired in with The Jigfield Follies, a variety show that featured eccentric novelty clarinetist Wilton Crawley. Valentine first performed with the company at the Washington Theatre, then followed the show to New York City.

Early in 1928 Valentine formed a ten-piece band in Indianapolis and called them the Patent Leather Kids. Just when the Kids were starting to get gigs locally, Valentine took off with his trombonist, Wheeler Moran (later known as Doc Wheeler), to work with Bernie Young's orchestra at the Wisconsin Roof in Milwaukee, performing with excellent musicians like Preston Jackson and Eddie Barefield. Valentine began to earn himself a reputation in Chicago by gigging with George Mitchell, Bob Shoffner, Jabbo Smith, and Carroll Dickerson. Before the year was up, Valentine was a member of Horace Henderson's orchestra, based at that time in Columbus, Ohio. In 1929 he toured the East Coast as a member of the Hardy Brothers' band, a group that operated out of Richmond, Virginia.

By early October 1929 Valentine was back home again in Indiana, making a series of recordings for the Gennett label with his Patent Leather Kids, now reduced to a trio. Valentine played trumpet, James Slick Helms was at the piano, and Paul George operated the banjo. Of 14 sides recorded on October 2, 1929, four featured vocals by Horace Smith and six by Hattie Snow. Two of the instrumentals, "Rock and Gravel" b/w "Jelly Bean Rag" (otherwise known as "Jelly Bean Drag") were also issued on the Champion label by "Skillet Dick His Frying Pans". During the remainder of 1929, Valentine played in a band led by Speed Webb.

He managed to work fairly regularly throughout the first half of the 1930s, most importantly with Lucky Millinder, Earl Hines, Tiny Bradshaw, and Elmer Calloway. He married in 1935, spent a few years living in Brooklyn, New York, then moved back to Indianapolis during the Second World War. Valentine spent the rest of his life in his hometown and died there in 1993. ~ arwulf arwulf, Rovi