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Croton’s Ann Hampton Callaway, The Diva Next Door

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It’s 7:30 one Thursday evening at Dizzy’s Club Coca-Cola, an intimate Lincoln Center jazz venue in the Time Warner Center. The showpiece of the sophisticated setting is a breathtaking view of Central Park through floor-to-ceiling windows behind the stage, with the skyline glittering like so many samples from the City’s Diamond District. But even the view can’t distract from the remarkable artistry of jazz/pop singer and songwriter Ann Hampton Callaway in a concert celebrating From Sassy To Divine: The Sarah Vaughan Project, the album she recorded here last year. For an hour or so, the Croton-on-Hudson resident treats the sold-out crowd to lush renditions of such Vaughan signatures as “Send in the Clowns” and “I’m Gonna Live Till I Die.” The dark-haired, statuesque Callaway—Jimmy Choo slingbacks add 5 inches to her natural 5’10” height—commands the stage with a vocal instrument the New York Times called “so rich, flexible and extravagantly gorgeous that it hardly matters what use she puts it to.” 

It’s practically impossible not to like Callaway—she’s warm, funny, and totally approachable. She answers questions about her stage outfit with an easy laugh. The flowing black sequined top is actually part of an outfit bought at Elephant’s Trunk in Mount Kisco, and the swishy palazzo-style pants are from “Needless Markup,” says Callaway, who adds that she also shops Nordstrom Rack for her “diva threads.”

Finding a time to speak with Callaway is an exercise in calendar juggling. She is one very, very busy “singer/songwriter/composer/lyricist/actress/pianist/performer.” The month before we chatted on the phone, she’d traveled to Vail, New York City, Palm Beach, and Boston before heading off to London and South Africa. But even just a day after her return from overseas, she’s upbeat and unfailingly gracious.

Given her wide-ranging list of professional accomplishments—she’s done everything from writing and singing the theme song for the Fran Drescher television series The Nanny to being the only composer to ever collaborate with Cole Porter—it’s hard to imagine anything musically she can’t do. “I’m not a good sight-reader at all,” Callaway admits. “But that never stopped Stevie Wonder.” Similarly witty is her response to a question about one thing people would be surprised to learn about her: “That I’m the love child of Lionel Hampton and Cab Calloway.” Callaway’s real parents are the late John Callaway, a well-known Chicago journalist, and Shirley Callaway, a singer and New York City vocal coach; her sister is the singer and actress Liz Callaway, a Croton resident with whom she often performs. The sisters even recorded a song together on Liz’s holiday EP, released in December.

One of Callaway’s earliest musical memories is feeling transported by Judy Garland singing “Over The Rainbow” on the family’s tiny black-and-white TV. The Callaway house was filled with music, and little Ann loved singing along to the family’s record player. After graduating high school, she “served two years” as an acting major at the University of Illinois. But the school wasn’t the right fit, and so she headed to Manhattan in 1979 to pursue her professional dreams; Liz joined her days later. To celebrate, they went to a nearby piano bar. When someone requested the song “Sometimes When We Touch” and the performer said he didn’t know it, Callaway piped up that she did; when he said he couldn’t play it, she said she could—and then she did. “I put everything I had into that song,” she recalls. Hired to play there for six hours a night, Callaway only knew 25 songs at the time, so she had to learn lots of others quickly. With no piano in her hotel room, she pretend-played on a make-believe keyboard. The upshot? Unlike most other aspiring performers, she says, “I never had to wait tables.”

Her career would grow to include extensive credits in just about every genre and venue. For starters, she’s starred on Broadway—she was nominated for a Tony and won a Theatre World Award for her performance in Swing!—and she has composed more than 250 songs for television, stage, and film. Her music and lyrics have been performed and recorded by Barbra Streisand (Callaway penned multiplatinum hits for seven of her recent CDs), Liza Minnelli, Michael Feinstein, and Carole King, whose album Tapestry inspired her own career. Callaway and King even wrote the spectacular hit “Tonight You’re All Mine” together. And wait, there’s more—Callaway appeared in The Good Shepherd for her feature film debut opposite Angelina Jolie and Matt Damon, and she has been invited for guest performances for President Clinton and for Mikhail Gorbachev’s Youth Peace Summit in Moscow.  

Flash forward to 2006 in Tucson, Arizona, where Callaway was performing with a local theater company. It was love at first sight, she says, when she met her now-wife, Kari Strand. Today Strand, who says she had a dream about meeting a brunette love two nights before she was actually introduced to Callaway, travels with Callaway as her road manager. It was their relationship that brought them to Croton—where Liz and her family also live—in 2007. “We wanted to have space and make a lovely new nest together,” Callaway explains. The pair, who married this past November, got the “this is it” feeling when first shown a brand-new, open plan Colonial. “It’s a little more traditional than we might have chosen,” says Callaway, “but we infused our eclectic, artsy style throughout.” 

They love that the area “draws a lot of artists and performers and has a warm, inclusive, down-to-earth feeling,” she adds. In addition to next-door neighbors Mark Mitchell, a pianist and conductor, and his wife Betsy Joslyn, a singer and actress, Callaway counts a TV producer, artists, singers, and even a handweaver for the Metropolitan Museum of Art as neighbors. “Everyone looks out for each other,” she says. “It feels like living in the 1950s.”

Not surprisingly, the indefatigable Callaway still has professional challenges on her wish list including playing a “juicy” book role in a musical, writing a Broadway show, and recording an all-original album. And she’s currently working on a radio show celebrating contemporary singers. Meanwhile, back at Dizzy’s, Callaway’s favorite quote, by André Gide, comes to mind: “Art is the collaboration between God and the artist, and the less the artist does the better.” Clearly, Callaway’s less is very much more indeed.