A native of Chicago, her father, John Callaway, was a journalist and her mother is a singer, pianist, and vocal coach. She learned scat singing from her father and a love of jazz from his record collection, and she learned classical music from her mother. Her sister, Liz Callaway, is a singer and actress on Broadway. Callaway performed in musicals at New Trier High School in Winnetka. After graduation, she studied acting for two years at the University of Illinois at Urbana-Champaign. She moved to New York City in 1979. During the 1980s, she worked as a cabaret singer accompanying herself on piano, performing jazz, traditional pop, and standards from the Great American Songbook.
While contributing to a CD reissue of songs by Cole Porter, she received permission from the Porter estate to compose music for his unrecorded song, "I Gaze in Your Eyes." The song was included on her debut album, which was released in 1992. A year later, she wrote and performed the theme song for the TV show The Nanny.
In addition to the theme for The Nanny, she wrote theme songs for Day's End, Cabaret Beat, and The Jim J and Tammy Fay Show and composed incidental music for the play, Baltimore Star by David Weiner. Her song "Manhattan in December" was included in the 2005 off-Broadway musical revue A Broadway Diva Christmas.
She composed "At the Same Time" for Barbra Streisand. The song appeared on Streisand's album, Higher Ground, which debuted at No. 1 and gave Callaway her first platinum record. Streisand asked her to write lyrics to a Rolf Lovland melody which she entitled "I've Dreamed of You" which Streisand sang to James Brolin at their wedding. The song was later recorded on her album, A Love Like Ours, released as a single, and selected for the album, The Essential Barbra Streisand. Streisand performed both songs on her live double album, Timeless. She chose Callaway's song "A Christmas Lullaby" for her album Christmas Memories.
Callaway's music and lyrics have also been recorded and performed by Karrin Allyson, Liz Callaway, Barbara Carroll, Blossom Dearie, Michael Feinstein, Harvey Fierstein, Carole King, Patti LuPone, Amanda McBroom, Donna McKechnie, Liza Minnelli, Peter Nero, and Lillias White.
In September 2005, Callaway performed her song "Let the Saints Come Marching" on a national TV broadcast on the Fox News Channel. She wrote the song in honor of victims of Hurricane Katrina. Her song "Who Can See the Blue the Same Again?" was released earlier in 2005 to raise money for survivors of the 2004 Indian Ocean earthquake and tsunami.
After the September 11 attacks, she composed "I Believe in America" and performed it on Larry King Live. Around the same time, she wrote "Let Us Be United", which was inspired by an 8,000-year-old prayer from the Rigveda. She recorded the song with Kenny Werner, the Siddha Yoga International Choir, and five-year-old Sonali Beaven, who sang in honor of her father who lost his life on Flight 93. It was released on CD and DVD to benefit Save the Children and the PRASAD Project.
She appeared in the movie The Good Shepherd and in Volare for Jim Henson Productions, directed by Tamela D'Amico. Her voice has been heard in TV jingles and voice-overs, including spots for Coca-Cola, Ethan Allen, and State Farm. She has done extensive broadcasting for Sirius Satellite Radio as a performer, DJ, and interviewer.
She produced Singer's Spotlight with Ann Hampton Callaway featuring Liza Minnelli and Christine Ebersole. She starred in Midnight Swing for the PBS television special Live from Lincoln Center and was featured in another PBS special with Keith Lockhart and Boston Pops. She has also performed for the Macy's Fourth of July Fireworks Spectacular and has made two appearances on Macy's Thanksgiving Day Parade.
For her work in the musical Swing!, she received a Tony Award nomination for Best Featured Actress in a Musical and won the Theatre World Award for "Outstanding Broadway Debut". She has received fifteen MAC Awards from the Manhattan Association of Cabarets & Clubs, two Backstage Bistro Awards, the 2005 Nightlife Award, the Johnny Mercer Songwriter Award, and the Norman Vincent Peale Award for Positive Thinking. In 2015, she was nominated with her sister Liz for a BroadwayWorld.com Award for their show Sibling Revelry.
She performed for U.S. President Bill Clinton in Washington, D.C. and was the invited guest performer for Soviet General Secretary Mikhail Gorbachev's Youth Peace Summit in Moscow in 1988.
Other Awards Ann has received
2013 "The Streisand Songbook" won two Broadwayworld.com Awards and the MAC Award for Show of the Year.
2014 BroadwayWorld New York Cabaret Award for "Performer of the Year"
2016 Broadway World New York Cabaret Award "Best Jazz Vocalist"1992 Ann Hampton Callaway (DRG)
1994 Bring Back Romance (DRG)
1996 Sibling Revelry (DRG) with Liz Callaway
1996 To Ella with Love (Sin-Drome)
1997 After Ours (Denon)
1997 White Christmas (Capitol)
1998 This Christmas (Angel)
1999 Easy Living (Sin-Drome)
2000 Swing! (Original Broadway Cast)
2002 Signature (N-Coded)
2004 Slow (Shanachie)
2006 Blues in the Night (Telarc)
2009 At Last (Telarc)
2011 Boom! Live at Birdland (PS Classics)
2014 From Sassy to Divine: The Sarah Vaughan Project (Shanachie)
2015 The Hope of Christmas (MCG Jazz)
With Liz Callaway1993 Anywhere I Wander: Liz Callaway Sings Frank Loesser
2001 The Story Goes On: Liz Callaway On and Off Broadway
2009 Passage of Time
With others1993 Live at Fat Tuesday's: May 13–15, 1993, Jay Leonhart
1995 Shoestring Revue (Original Cast)
1996 This Life, Her Songs & Her Friends, Portia Nelson
2000 Swing! (Original Broadway Cast)
2000 Far from the Madding Crowd (cast recording), Gary Schocker
2003 Holiday Pops!, Peter Nero
2004 Fine and Dandy (Original Broadway Cast)
2005 In Good Company, Lee Lessack
2005 Ladies Sing for Lovers, Frank Mantooth
2006 Christmastime Is Here, Cincinnati Pops Orchestra/Erich Kunzel (Telarc)
2007 The Good Shepherd (soundtrack), Marcelo Zarvos
2007 Loungin at Redkliff: Kampengrooves, Ive Mendes
2008 The Traveler, Kenny Barron (Sunnyside)
2012 Live, Scott Alan
2016 The Gold Standards, Deborah Silver