Taking a Chance on Love is an album by American jazz singer Jane Monheit that includes cover versions of standards and songs from musicals. The album was released on September 7, 2004, via Sony Classical label.
This was Monheit's fifth album and fourth studio album, her first album with Sony. Taking a Chance on Love was her first collaboration with Grammy Award-winning producers Peter Asher and Al Schmitt. She sang on the album Session 55 by Les Brown, which Schmitt produced.
During the album's first week of release, it entered the pop chart on Billboard magazine and reached number one on the Traditional Jazz chart. The song "Dancing in the Dark" received a Grammy Award nomination for Best Instrumental Arrangement Accompanying Vocals.
Monheit recorded "Honeysuckle Rose" with Wynton Marsalis on the album ' by Mark O'Connor. The bonus track "Over the Rainbow" appeared on the soundtrack Sky Captain and the World of Tomorrow. The bonus track "I Should Care" is from Legends of Jazz with Ramsey Lewis: Season One, Vol. 2 (2006).
A four-track EP and a two-track EP release of Monheit's album Taking a Chance on Love were released as limited editions in 2004.