Background: Herb Jeffries (born Umberto Alexander Valentino; September 24, 1913 - May 25, 2014) was an African-American actor of film and television and popular music and jazz singer-songwriter, known of his baritone voice. He was of African descent and Hollywood's first singing black cowboy. In the 1940s and 1950s Jeffries recorded for a number of labels, including RCA Victor, Exclusive, Coral, Decca, Bethlehem, Columbia, Mercury and Trend. His album Jamaica, recorded by RKO, is a concept album of self-composed calypso songs.
Context: From Detroit, at the urging of Louis Armstrong, Jeffries moved to Chicago where he performed in various clubs. One of his first gigs was in a club allegedly owned by Al Capone. Jeffries began his career working with Erskine Tate and his Vendome Orchestra. Tate signed the 19-year-old Jeffries to a contract with his Orchestra at the Savoy Ballroom in Chicago. His break came during the 1933 Chicago World's Fair A Century of Progress International Exposition singing with the Earl Hines Orchestra on Hines' national broadcasts live from the Grand Terrace Cafe. His first recordings were with Hines in 1934, including "Just to be in Carolina". By 1940, he was singing with the Duke Ellington Orchestra and then recorded with him from 1940 to 1942. His 1940 recording of "Flamingo" with Ellington, released in 1941, sold more than 14 million copies in its day. His name had been Herbert Jeffrey, but the credits on the record mistakenly called him Jeffries, so he renamed himself to match the typo. "Flamingo" was later covered by a white singer, the popular vocalist Tony Martin. During his time with the Duke Ellington Orchestra as a lead vocalist, Jeffries proved his talent as a mature singer, demonstrating his wide vocal range in such songs as "I Don't Know What Kind of Blues I've Got," "The Brownskin Gal," and "Jump for Joy" (all 1941). The 1944 single "My Little Brown Book" by Ellington and his Famous Orchestra, on which Jeffries provided vocals, reached No. 4 on Billboard R&B chart. Later on, Jeffries was replaced in the Ellington's band by Al Hibbler.  In his teens, Jeffries had developed a fine voice, initially singing in higher registers. He started out his singing career as a lyrical tenor, but, on the advice of Duke Ellington's longtime music arranger, Billy Strayhorn, he lowered his range to mimic the vocal stylings of crooner Bing Crosby. Jeffries became a "silken, lusty baritone," according to music critic Jonny Whiteside.  In 1945, Jeffries had a hit on the Billboard R&B chart with "Left A Good Deal In Mobile" (No. 2), on which he was accompanied by pianist Joe Liggins and his band Honeydrippers. Then, he moved to Europe and performed there for many years, including at nightclubs he owned. He was back in America by the 1950s, recording jazz records again, including 1957 collection of ballads, Say It Isn't So.  In 1995, at age 81, he recorded The Bronze Buckaroo (Rides Again), a Nashville album of songs on the Warner Western label.
Question: What did he gain with his big break?
Answer: In 1945, Jeffries had a hit on the Billboard R&B chart with "Left A Good Deal In Mobile" (No. 2), on which he was accompanied by pianist Joe Liggins

Problem: Background: Hunter was born in New York City, the son of Gertrude (nee Gelien) and Charles Kelm. His mother, from Hamburg, was a German Roman Catholic immigrant, and his father was Jewish. Hunter's father was reportedly abusive, and within a few years of his birth, his parents divorced. Tab grew up in California with his mother, older brother Walter, and maternal grandparents, John Henry and Ida (nee Sonnenfleth)
Context: Hunter had a 1957 hit record with the song "Young Love," which was No. 1 on the Billboard Hot 100 chart for six weeks (seven weeks on the UK Chart) and became one of the larger hits of the Rock 'n' Roll era. It sold over one million copies, and was awarded a gold disc by the RIAA.  He had the hit, "Ninety-Nine Ways," which peaked at No. 11 in the US and No. 5 in the UK. His success prompted Jack L. Warner to enforce the actor's contract with the Warner Bros. studio by banning Dot Records, the label for which Hunter had recorded the single (and which was owned by rival Paramount Pictures), from releasing a follow-up album he had recorded for them. He established Warner Bros. Records specifically for Hunter.  Hunter's acting career was also at its zenith. William Wellman used him again in a war film, Lafayette Escadrille (1958). Columbia Pictures borrowed him for a Western, Gunman's Walk (1958), a film that Hunter considers his favorite role.  Hunter starred in the 1958 musical film Damn Yankees, in which he played Joe Hardy of Washington, D.C.'s American League baseball club. The film had originally been a Broadway show, but Hunter was the only one in the film version who had not appeared in the original cast. The show was based on the 1954 best-selling book The Year the Yankees Lost the Pennant by Douglass Wallop. Hunter later said the filming was hellish because director George Abbott was only interested in recreating the stage version word for word.  He also starred in They Came to Cordura (1959), with Gary Cooper and Rita Hayworth. Sidney Lumet starred him opposite Sophia Loren in That Kind of Woman (1959).
Question: Did "ninety-nine ways" make the charts?
Answer:
which peaked at No. 11 in the US and No. 5 in the UK.