Famous Jazz Singers and Entertainers from the Rat Pack and the Middle of the Road

TONY BENNETT

Multiple Grammy winner Tony Bennett was still in high school when he started out crooning in small New York clubs as Joe Bari. Bob Hope liked his sound but not his stage name. Upon learning that Joe had been born Anthony Dominick Bendetto, Hope suggested that the young man merely simplify his own real name. The master comic then strolled onto the Brooklyn Paramount stage and, for the first time, introduced the world to Tony Bennett. More than 50 hits followed between 1951 and 1977. Tony never warmed to the music that pushed him off the charts, insisting that “rock ‘ n’ roll doesn’t have a note of real feeling.” He preferred his kind of “quality songs” -- the ‘30s and ‘40s tunes of Richard Rodgers and Lorenz Hart, Cole Porter, Irving Berlin, George Gershwin and other Tin Pan Alley composers. Ironically, two of Bennett’s sons later formed their own rock band -- and Tony himself made a major comeback with younger audiences in the ‘90s, still singing his beloved standards. His 1994 “MTV Unplugged” album became one of his all-time best-sellers and won the Grammy for Album of the Year.

Biggest hits: BECAUSE OF YOU (1951), COLD COLD HEART (1951), RAGS TO RICHES (1953)

PAT BOONE

Only one other star -- Elvis Presley -- outranked Pat Boone as a hitmaker in the latter half of the 1950s. Between 1955 and 2002, Pat placed no less than 67 songs on the charts, including 16 in the Top 10. His sales topped 45 million and he holds the all-time record for consecutive weeks on the hit parade: more than 200. In 1957, Boone became the youngest performer in history to host his own prime-time variety TV series. It was also the year in which Pat starred in the first of his 15 films. He eventually became a best-selling author, talk show host, inspirational leader and, in 1997, the first 63-year old to release a hit CD of heavy metal music (“No More Mr. Nice Guy”; heavy mental songs re-arranged into big band music). From the start, Boone was always “Mr. Nice Guy” -- a modest, charming, extremely likeable entertainer and individual -- “the clean-cut alternative to Elvis Presley’ (although the two were actually good friends). Pat’s warm, mellow, perfectly-pitched baritone proved equally adept at tender ballads, heartfelt hymns, Christmas classics, country standards, rock ‘n’ roll and rhythm ‘n’ blues.

Biggest hits: LOVE LETTERS IN THE SAND (1957), DON’T FORBID ME (1956), APRIL LOVE (1957)

MICHAEL BUBLE

Unlike other kids in the ‘80s and ‘90s, Michael Buble (pronounced BOO-BLAY) spent his childhood listening to Ella Fitzgerald, Sarah Vaughan, Rosemary Clooney and Frank Sinatra. “My grandfather was really my best friend growing up,” said the Vancouver vocalist. “He was the one who opened me up to a whole world of music than seemed to have been passed over by my generation. Although I like rock ‘n’ roll and modern music, the first time my granddad played me the Mills Brothers something magical happened. The lyrics were so romantic, so real -- the way a song should be. It was like seeing my future flash before me. I wanted to be a singer and I knew that this was the music that I wanted to sing.” Buble entered a local talent competition and won first place -- only to be disqualified for being under age. After turning 17, Michael won the top prize again -- this time in the Canadian Youth Talent Search. He recorded a series of independently-released albums before Grammy winner David Foster, the owner of Canada’s 143 label, signed the young man and directed the production of his debut album in 2001. Included was what would become the typical mix of numbers on a Buble album -- some all-time standards (“For Once in My Life,” “The Way You Look Tonight”) plus newer titles (like “You’ll Never Find Another Love Like Mine”). The Bee Gees even sang along on Buble’s remake of their 1971 hit “How Can You Mend A Broken Heart.” “Michael hasn’t just learned this music, said Foster. “He’s lived it. He brings youthful energy to it -- tough and tender at the same time -- like nothing else I’ve ever heard. The great thing is, he’s tapped into a repertoire that can last him 50 years. He’s at the beginning of a very long career.”

Biggest hits: HOW CAN YOU MEND A BROKEN HEART? (2003), HOME (2005), SAVE THE LAST DANCE FOR ME (2006)

NAT “KING” COLE

His voice was as tender as a lover’s touch -- warm, caressing, silky soft, as smooth as velvet -- and over a 30-year recording career he became one of the best-loved romantic balladeers of all time. Nathaniel Adams Coles was born the son of a Baptist minister in Montgomery, Alabama in 1917 and by age five was playing the piano. Fifteen years later, after “King” had been added to his name as a variation on the fairy tale figure Old King Cole (and the “s” in Coles dropped), Nat still thought of himself as strictly an instrumentalist. That changed after a club patron insisted one night that he both play and sing a request. To Cole’s amazement, it was his voice that swept him to fame in 1942 and kept him on top until his death at age 48 from lung cancer. Nat made movies, hosted his own TV show and scored more than 175 pop and rhythm ‘n’ blues (R&B) hits. A quarter century after his death, Nat “King” Cole won a Lifetime Achievement Grammy Award. The next year, an electronic “duet” between Nat and his now grown-up daughter, Natalie, became both a Grammy winner and million-selling sensation.

Biggest hits: TOO YOUNG (1951), MONA LISA (1950), FOR SENTIMENTAL REASONS (1946)

PERRY COMO

Perry Como was making $40 a week as a barber in 1933 when he got an offer to sing with a local big band for $28 a week. Never one to pass up a good clip job, he said yes --- and three years later did the same when given the opportunity to join Ted Weems’ nationally-known orchestra. After Weems broke up his big band in order to enlist for World War II, Perry went solo as both a radio star and a recording artist. Between 1943 and 1974, Como logged almost 150 hits, everything from neo-opera to novelties, Christmas carols to country classics, beautiful ballads to sacred songs, romantic rhapsodies to rock ‘n’ roll records. Over a 50-year career, Perry’s total record sales topped 100 million -- and from the ‘50s to the ‘80s, he was a top TV star who won five Emmys. The ex-barber’s style was so relaxed and easygoing that comedians loved to parody him as “Perry Coma.” He’d just smile and add a few self-depreciating remarks of his own. We lost the man Andy Williams said had “the sweetest, loveliest voice of any pop singer” in 2001, when Perry died at the age of 88.

Biggest hits: SOME ENCHANTED EVENING (1949), PRISONER OF LOVE (1946), ROUND AND ROUND (1957)

BING CROSBY

Harry Lillis Crosby was, without a doubt, the most popular entertainer of the pre-rock ‘n’ roll years. He got his unusual nickname as a child in Tacoma, Washington, where he was born in 1901. As his prominent ears resembled those of a character in a comic strip called “The Bingville Bugle,” he was then and forevermore known as “Bing.” Over a full half-century, Bing Crosby starred on radio, TV, in concert and in more than 50 movies -- and was planning more at the time of his passing in1977. His resonant baritone was warm, deep and rich, allowing him to singing rhythmically as well as any musician could play. “He called it groaning,” said Bob Hope, “but we call it magic.” Bing’s music ranged from serious songs to comedy cavalcades -- yet Crosby could send home a tender romantic verse with all the heart and soul anyone could possibly wish for. And he certainly loved to swing, always preferring to work in front of a full, live orchestra. Between 1927 and 1965 Bing cut over 350 (!) hits -- more than anyone else ever.

Biggest hits: WHITE CHRISTMAS (1942), SWINGING ON A STAR (1944), I’LL BE SEEING YOU (1944)

VIC DAMONE

“Romance is my life,” said Vic Damone, “and music and love are together.” Born Vito Rocco Farinola in 1928 in Bensonhurst, a neighborhood in Brooklyn, Vic Damone delivered fruit and sang in his church choir before landing the job that turned his life around -- working as a theatre usher. One night he worked a Frank Sinatra concert as was mesmerized by “his phrasing, his breathing, his tone, his timbre. Everything.” Having discovered a role model, Damone decided to try making it as a supper club crooner. He won an Arthur Godfrey “Talent Scouts” competition in 1946 and the next year had both a contract with Mercury Records and his own radio program. Fifty hits followed through the end of the ‘60s, as well as movie roles and jobs hosting three different TV series. Vic’s liquid baritone and serene delivery made him one of the most popular of all postwar romanticists. “I’m a ballad singer,” said Damone, “and I guess I always will be.” Frank Sinatra himself credited Vic with having “the best pipes in the business.”

Biggest hits: YOU’RE BREAKING MY HEART (1949), MY TRULY TRULY FAIR (1951), ON THE STREET WHERE YOU LIVE (1956)

DICK HAYMES

Dick Haymes had a voice deeper and more resonant than Sinatra’s -- one heavily influenced by his idol, Bob Eberly, who was the top male crooner with the big band of Jimmy Dorsey. Haymes was a charming, intelligent singer-songwriter whose sensitive sound made him one of the 1940s’ best-loved entertainers. Born in Buenos Aires, Argentina in 1916, Dick grew up in the U.S., where his mother, a renowned vocal coach, taught him every nuance of his craft. His first break came in 1940, when he began a two-year run with the orchestra of Harry James. Then came stints with the big bands of Benny Goodman and Tommy Dorsey. Finally, in 1943, Dick emerged on his own, racking up 66 hits over the next 13 years. They included ten duets with Helen Forrest, his co-star on one of his radio series. Haymes made many movies between 1944 and 1953 and was married six times -- to lovely ladies like Joanne Dru and Rita Hayworth. His career declined in the ‘50s, contributing to his alcohol abuse and eventual bankruptcy. His last wife, Wendy, rescued him from that and in the ‘70s Haymes returned as a popular club and TV performer and made some first-rate new recordings. He died in 1980.

Biggest hits: LITTLE WHITE LIES (1948), YOU’LL NEVER KNOW (1943), IT CAN’T BE WRONG (1943)

ENGELBERT HUMPERDINCK

Although born in Madras, India, in 1936, Arnold Dorsey grew up in England, where he paid for his singing lessons as a teenager by delivering papers for 72 cents a week. His attempts at crooning in workingmen’s clubs were all financial failures; in fact, in 1959 young Dorsey was diagnosed with tuberculosis, brought on by starvation and sleeping on floors or open ground. Finally, in 1965, Gordon Mills, the manager of Tom Jones, signed Arnold and immediately changed his name to that of a 19th century German composer whose best-known work was the folk opera “Hansel and Gretel.” “I was sitting on a stool at the time,” recalled the six-foot, three-inch singer, “and I laughed so hard I fell off. I thought he was joking.” Mills wasn’t -- and over the next 18 years the man he dubbed “Engelbert Humperdinck” became famous as the “King Of Romance” with ten gold albums and nearly two dozen hits in the ‘60s, ‘70s and ‘80s.

Biggest hits: RELEASE ME (1967), AFTER THE LOVIN’ (1976), WINTER WORLD OF LOVE (1969)

DEAN MARTIN

Twinkle-eyed romantic Dean Martin spent a decade paired with crazy Jerry Lewis as the ‘50s’ most madcap comedy team. After each went solo, “Dino” became the host of his own top-rated TV series and the maker of dozens of sometimes swingin’, sometimes heartwarming hits. In his movies, nightclub and TV appearances, and 60-plus albums, the former Dino Crocetti cultivated a suave, effortless pose. “I don’t work at nothin’;” Martin boasted to Look magazine in 1966. “I’m not a great singer or anything like that. I just croon.” Martin began his show business career at age 17, singing in Ohio nightclubs near his hometown. He was noticed by Cleveland bandleader Sammy Watkins, who hired Martin as his band’s featured vocalist. In1944 Dino was given his own 15-minute radio program, “Songs by Dean Martin,” which was broadcast from New York City. In 1946 he recorded for the very first time: four songs for Diamond Records. During a club engagement that year, Martin met Lewis and they teamed up, with Dean playing the straight man to Jerry’s clown. Their immense club popularity led to radio and TV appearances as well as 16 films between 1949 and 1956. After the duo split up, Martin found solo stardom in movies, on record (for Capitol and Reprise) and in concert. To his many fans, Dino was the epitome of “cool,” with a cigarette in one hand and a bit o’ booze in the other. (In reality, Martin never really was much of a drinker. That “whiskey” in his glass was actually apple juice.) Dino died on Christmas Day, 1995.

Biggest hits: MEMORIES ARE MADE OF THIS (1955), EVERYBODY LOVES SOMEBODY (1964), THAT ’S AMORE (1953)

JIM REEVES

The youngest of nine children, James Travis Reeves hosted and sang on his own weekly radio show over Shreveport’s KRMD while in high school. After his dreams of becoming a professional baseball player ended with a leg injury, Jim decided to stick with radio and slowly developed a warm, intimate microphone technique. He was still announcing on “The Louisiana Hayride” and other radio shows when he turned 30 in 1953. Now and then, when an artist failed to show up on time, Jim would sing on the live “Hayride” broadcast. Producer Fabor Robinson happened to be listening one night and offered Reeves a contract with Abbott Records. That May, Jim topped the country charts with “Mexican Joe,” his first of 80 hits over the next three decades. What makes that accomplishment especially mind-boggling is that 37 of those hits -- nearly half of Reeves’ career total -- reached the hit parade during the 20 years after his death at age 40 in a 1964 plane crash. How was that possible? It helped that Jim was a prolific recording artist -- and that his label took great pride in slowly releasing his tunes from their vault as 45 RPM singles. Add to that the fact that, after 1955, Reeves’ records were released by RCA Victor and produced in a timeless style by Country Music Hall of Famer Chet Atkins. Chet encouraged Jim to sing softly and intimately, very close to the mike, in the lower baritone range of his velvet voice. And the backup musicians played Atkins’ new ”Nashville Sound” arrangements, which were far more uptown and pop-sounding than country’s old hillbilly style. That helped “Gentleman Jim,” who was elected to the Country Music Hall of Fame himself in 1967, to score big hits in the pop field as well.

Biggest hits: HE’LL HAVE TO GO (1959), FOUR WALLS (1957), AM I LOSING YOU (1960)

KENNY ROGERS

“I’m not a great singer or vocal technician,” said Kenny Rogers. “I’m a stylist. I have a familiar voice with a certain honesty and distinction.” His voice became familiar through nearly 70 pop and/or country hits from the ‘60s through the ‘90s. Born in Texas, Kenny was six in 1944 when he made his singing debut before a nursing home audience. He cut his first single with his high school band, The Scholars, in 1956. Stints in a jazz quartet (The Bobby Doyle Four) and a folk group (The New Christy Minstrels) followed before Kenny finally scored as lead singer of The First Edition in 1968 (“Just Dropped In” and others). After 11 hits and their own TV series, The First Edition broke up in 1976. Rogers then embarked on a solo career as a country star -- one of the few channels then open to someone of his “advanced” age (38). The results exceeded his wildest expectations -- as Kenny emerged as both a country and pop superstar, leading to film roles in the “Gambler” series of movies and “Coward of the County.” After some fallow years in the late ‘80s and ‘90s, Rogers made a spectacular comeback in 1998 by launching his own label (Dreamcatcher Records) and releasing the #1 country hit “Buy Me A Rose.”

Biggest hits: LADY (1980), COWARD OF THE COUNTY (1979), SHE BELIEVES IN ME (1979)

FRANK SINATRA

After less than one year in the employ of big band leader Harry James, a skinny singer named Francis Albert Sinatra was given the break of a lifetime: to sing with the third most popular band of 1939 (Artie Shaw’s was #1, Kay Kyser’s was #2). Almost overnight, the combination of the man they’d call “The Voice” with the orchestra of “That Sentimental Gentleman of Swing,” Tommy Dorsey, sent the music world swooning. “No singer had ever sung like that before, recalled Jo Stafford, then a member of the Pied Pipers, the vocal quartet which often backed Sinatra. By the time he left Tommy’s organization in 1942, Frank was a superstar. He would go on to make his mark as an Oscar-winning actor, TV host, record company owner and the creator of some 170 solo (and duet) hits through 1980. Among Sinatra’s Grammys was a somewhat premature 1965 “Lifetime Achievement Award,” as he had yet to chart 30 more albums (13 of which became million-sellers!). By that time billed as “The Chairman of the Board,” “The Voice” continued to enchant millions with new material until just before his death in1998 at the age of 82.

Biggest hits: ALL OR NOTHING AT ALL (1943), FIVE MINUTES MORE (1946), LEARNIN ’ THE BLUES (1955)

MEL TORME

“Though I love to write music, arrange songs, play drums, author books and act, first and foremost I’m a singer,” said Mel Torme. “It’s what I do best.” Born in Chicago, Mel made his radio singing debut in 1929 -- wearing a sailor suit and singing “You’re Driving Me Crazy.” He was four years old. Later, in the school band, he played alongside future TV legend Steve Allen. “Singing with the Chico Marx orchestra was my first big break,” Torme recalled. The next year, at age 16, he made his film debut in the 1946 Frank Sinatra musical “Higher and Higher.” It was DJ Fred Robbins who first called Mel “The Velvet Fog,” an improvement over such earlier nicknames as “Mr. Butterscotch” or “The Kid with Gauze in his Jaws.” “I really detested it,” said Mel, of the “Velvet Fog” tag. Over time, though, he came to realize that “it really embodies me as a performer and personality.” Torme scored his dozen hits between 1945 and 1962, explaining that he was attracted to a tune “if it’s a great song with a pleasing melody and a strong backbone of lyrics.” As a composer, Mel is best-known for co-writing the Nat “King” Cole Yuletide classic “The Christmas Song (Chestnuts Roasting On An Open Fire).” Torme died at age 73 in 1999.

Biggest hits: CARELESS HANDS (1949), AGAIN (1949), BEWITCHED (1950)

ANDY WILLIAMS

If you’d been in the right church in Wall Lake, Iowa in 1937, you’d have heard Bob, Don, Dick and eight-year-old Andy harmonizing as The Williams Brothers. The quartet later sang on radio and records (backing Bing Crosby, for instance, on “Swingin’ On A Star”) and toured nightclubs with comedienne Kay Thompson. After that act broke up in 1953, Bob, Don and Dick retired from show biz, but not Andy. He began a three-year run as a regular on Steve Allen’s television program and started cutting his first of 45 hits through 1976. Williams also hosted his own TV variety series between 1962 and 1971. “I think you have to bear in mind that mine was not just a recording career but a television and recording career,” Andy said. “The two of them together, working hand in hand. Even in making records, our thought was, ’What can we do with this one to expose it well on TV’?” That philosophy certainly paid off, since -- in addition to his hit singles -- Williams scored 34 hit albums between 1960 and 1995.

Biggest hits: BUTTERFLY (1957), CAN’T GET USED TO LOSING YOU (1963), ARE YOU SINCERE (1958)