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The ninth of ten children born to Rodman Jacob Short, a coal miner, and Myrtle (Render) Short, a domestic, in Danville, IL, Robert Waltrip Short, nicknamed Bobby, took an early interest in the family piano and, despite a few lessons, was essentially self-taught. He began playing professionally in local roadhouses at the age of eight or nine. Soon, he was performing at society parties in a white tuxedo. In July 1936, when he was 11, he attracted the attention of booking agents who, with his mother's permission, took him to Chicago to perform in vaudeville and on radio. In June 1937, after finishing grade school, he traveled to dates in Cleveland and Toledo, then moved to New York City, where he appeared at the Frolics Cafe in October and at La Grande Pomme, as well as at other clubs and theaters around the country. He returned to Danville in the summer of 1938 to attend to high school and performed only in local venues over the next several years. But after graduating in 1942 he went back to show business permanently, opening at the Capitol Lounge in Chicago that July, followed by engagements in Cleveland, Omaha, and Los Angeles, where he settled in 1943. By the following year, however, he was working in Milwaukee and St. Louis, and in the spring of 1945 he was an opening act at the Blue Angel in New York City for four weeks. He then returned to California, by way of an appearance in Phoenix, where he performed at the Haig and the Café Gala over the next few years. While he was at the Haig, in the late '40s or early '50s, he made a record that was sold at the club. He also appeared without credit in the film musical Call Me Mister, released in January 1951, singing "Going Home Train."
In 1952, Short moved to Paris, where he appeared at the Mars Club and Spivy's, also playing at the Embassy Club in London over the course of the year. He returned to the U.S. for an engagement at the Black Orchid in Chicago, then went back to Los Angeles and the Café Gala, and made a 10" album, Bobby Short Loves Cole Porter, released by Atlantic Records. His first full-length LP, Songs by Bobby Short, recorded in March 1955, featured seven songs (out of 13) composed by Vernon Duke, who wrote its liner notes when it was released by Atlantic later that year. In February 1956, he began an 18-week engagement at the Beverly Club in New York City, which became his home. From May 9 to May 27, 1956, he made his Broadway debut in the City Center's limited-run revival of the Cole Porter musical Kiss Me, Kate, performing "Too Darn Hot" at the start of the second act. His second 12" LP for Atlantic, Bobby Short, was released in 1957, and at the same sessions in the late summer and fall of 1956, he recorded material for his third album, Speaking of Love, released in 1958. In the winter of 1956-1957, he appeared at the Red Carpet in New York, followed by an engagement at Le Cupidon. During the summer of 1957, Atlantic hired a horn section for what was intended to be a two-LP set, but only one disc, Sing Me a Swing Song, appeared as his fourth album in 1958. (The rest of the material was issued in 1971 as the LP Nobody Else But Me.)
Short returned to the Blue Angel with top billing and a salary of 1,000 dollars a week on November 14, 1957, continuing to appear at the club off and on until 1963. In late 1958 and early 1959, he recorded his fifth full-length Atlantic LP, The Mad Twenties, an album of songs from the 1920s. Meanwhile, he appeared at the Living Room, then at the Weylin Hotel, where, in March 1959, he recorded the live album Bobby Short on the East Side before moving on to the Arpeggio. He also worked in California, Florida, and Chicago during the summer in the early '60s. In March 1962, along with LaVern Baker and Chris Connor, he recorded an album of the score of Richard Rodgers' Broadway musical No Strings, billed as "An After Theatre Version." In June 1963, he recorded My Personal Property, an album of songs composed by pop and Broadway songwriter Cy Coleman. He gave his final performance at the Blue Angel on July 10, 1963, then moved to the Café Ambassador of the Sheraton East Hotel. In early 1964, he invested in a French restaurant, the Caprice, with Blue Angel co-owner Herbert Jacoby and began appearing there. It lasted only 15 months, and in 1965, having lost his savings in the venture, Short faced a career crisis brought on by the rise of television and rock & roll, trends that led to a decline in the nightclub business. He played where he could around the country, including stints in Provincetown, MA, and Chicago, and in the winter of 1965-1966 appeared in the second edition of Ben Bagley's off-Broadway revue, The Decline and Fall of the Entire World as Seen Through the Eyes of Cole Porter, at Square East in Greenwich Village. (The show was recorded live by Painted Smiles Records, and Short, temporarily free of his Atlantic Records contract, also made recordings for Bagley's series of various-artists composer collections, including Cole Porter Revisited, George Gershwin Revisited, Irving Berlin Revisited, Jerome Kern Revisited, and Rodgers and Hart Revisited, Vol. 2.) He then went into L'Intrigue, a club on West 56th Street, later returning to the Living Room. He appeared at Paul's Mall in Boston and spent ten weeks during the summer of 1966 at the Playboy Club in London. Also in 1966, he appeared in a television production of the musical revue Pins and Needles.
Short's luck finally turned in the spring of 1968. The Carlyle Hotel, looking for a substitute for pianist George Feyer, who had long reigned at its 120-seat Cafe Carlyle and was going on vacation, took the advice of Atlantic president Ahmet Ertegun and hired Short in the interim. He proved so popular that, when Feyer's contract expired, the Carlyle hired him as a permanent replacement, performing three shows a night eight months a year. (Later, it became two shows a night and two three-month stints in the fall and spring.) Meanwhile, he was second-billed to Mabel Mercer in concerts held at Town Hall in New York in May 1968 and recorded for a double LP by Atlantic, Mabel Mercer and Bobby Short at Town Hall. The shows were so successful that they were repeated the following year, resulting in a another two-LP set, Second Town Hall Concert. Atlantic renewed its association with Short and commissioned a new solo studio album, Jump for Joy, released in 1969. The 13-year-old Nobody Else But Me followed, and in 1972 Short took another crack at Cole Porter, this time recording a double LP that repeated the title of his two-decades-old 10" record, Bobby Short Loves Cole Porter. Amazingly, the album, supported by a concert appearance at New York's Avery Fisher Hall, reached the Billboard pop chart, and Atlantic followed with a series of two-disc collections: Bobby Short Is Mad About Noël Coward (1972); Bobby Short Is K-RA-ZY About Gershwin (1973); Live at the Cafe Carlyle (1974); and Bobby Short Celebrates Rodgers & Hart (1975). Meanwhile, he published a memoir of his youth, Black and White Baby (1971).
Over the years, Short came to represent the elegance and sophistication of New York with his tuxedoed appearance and repertoire of standards. As a result, he became attractive to advertisers, who frequently featured him in television commercials and print ads for such products as perfume and designer jeans. He also got other opportunities to perform. In February 1979, he acted in the ABC television mini-series Roots: The Next Generations, and in May 1980 he was a producer and participant in the Broadway revue Black Broadway, which had a brief run at Town Hall. His other TV guest appearances included the series The Love Boat, Tattingers, In the Heat of the Night, Central Park West, Frasier, and 7th Heaven. There were also films. He was seen and heard as himself, performing Cole Porter's "I'm in Love Again" at the Cafe Carlyle in Woody Allen's Hannah and Her Sisters in 1989, and his recording of Porter's "I Happen to Like New York" was heard over the titles of Allen's Manhattan Murder Mystery in 1993. (Other soundtrack-only appearances included Savages  and Love Affair .) He also appeared in the films For Love or Money (1993) and Man of the Century (1999), and in the TV movies Hardhat and Legs (1980), A Night on the Town (1983), and Blue Ice (1992). He published a second memoir, Bobby Short: The Life and Times of a Saloon Singer, written with Robert Mackintosh, in 1995.
On records, Short moved to Elektra/Asylum for 1982's Moments Like This (which reached the jazz charts), but returned to Atlantic for Guess Who's in Town: Bobby Short Performs the Songs of Andy Razaf (1987), a tribute to the little-known wordsmith who worked with Fats Waller and Eubie Blake. He didn't cut any new records for several years, but in the early '90s he signed with Telarc for a series of CDs starting with the live album Late Night at the Cafe Carlyle (March 1992), which reached the jazz charts and was nominated for the 1992 Grammy Award for Best Traditional Pop Vocal Performance, and including Swing That Music (August 1993), recorded with the Howard Alden-Dan Barrett Quartet; the live Songs of New York (1995); another jazz-chart entry, Celebrating 30 Years at the Cafe Carlyle (January 1998); How's Your Romance (January 1999); and You're the Top: The Love Songs of Cole Porter (June 1999). He switched to the audiophile Surrounded by Entertainment label for 2001's Piano, an album on which he performed mostly piano instrumentals. He sang the title song on clarinetist Ken Peplowski's 2004 album Easy to Remember.
Short announced his retirement from the Cafe Carlyle with his final appearance on New Year's Eve 2004, but later agreed to return in May 2005 to mark the club's 50th anniversary. Instead, he died of leukemia at the age of 80 on March 21, 2005. In a profile in The New Yorker magazine in December 1970, Whitney Balliett had described Short as "one of the last example (and indubitably the best) of the cafe singer or the supper-club singer or 'troubadour.'" Thirty-five years later, other examples had emerged, notably Michael Feinstein, Harry Connick, Jr., and Peter Cincotti. But Balliett's assessment that Short was the best of his time remained inarguable. ~ William Ruhlmann, Rovi