She has released records on Atlantic, Verve, and GroundUP and has sung with many artists including Rod Stewart, Barbra Streisand, Snarky Puppy, Celine Dion, Pink Martini, Gavin DeGraw, Joe Cocker, Chaka Khan, Nikka Costa, and Randy Jackson.

At the age of 16, Woodward was accepted to the Manhattan School of Music to study jazz, but after a year she decided to drop out to focus on songwriting and performing.

She spent the next few years in swing organ trios, including The Sugarman 3, working as a session singer, a waitress, and singing jazz standards in restaurants in Greenwich Village.

[8] During the following year, Woodward was asked by producer Jaime Houston to record the big-band tune "It's Oh So Quiet" for the Disney film Ice Princess; the song was later used in various TV shows, commercials, and the Birds of Prey trailer.

[10][11] It was produced by Itaal Shur and Tim K.[11] The song "Hot and Bothered" takes its melody from a Yiddish lullaby that Woodward's grandmother sang to her as a baby.

Originally called "More to Life", the song was written with Kevin Kadish and Sabelle Breer for Woodward's 2003 Atlantic debut but was released instead on the Japanese import version of the album as a bonus track.

[15][17][18] Woodward also appeared in the 2011 Garry Marshall film New Year's Eve where she played the backing vocalist for Jon Bon Jovi and Lea Michele.

[21][22][23][24] From 2012 to 2016 she worked as a background vocalist for Rod Stewart, singing on the albums Blood Red Roses, Another Country, Time, and Merry Christmas, Baby[9] as well as touring internationally with him, including at the 2015 BBC Music Awards.

[25] After Woodward, Holly Palmer, and songwriter Michelle Lewis first came together to sing at a Christmas Party in 2010, they decided soon after to write swing and boogie songs under the name The Goods.

[36] Both albums included songs by Blind Willie Johnson, Bessie Smith, En Vogue, Nina Simone, and Terence Trent D'Arby.

The album included bassist Tim Lefebvre (David Bowie, Tedeschi Trucks Band), drummer Amy Wood (Fiona Apple), and singers Gaby Moreno, Stevvi Alexander, and Holly Palmer.

[39] Woodward has also sung background vocals for Celine Dion, Rod Stewart, Carole King, Joe Cocker, Barbra Streisand, The Doobie Brothers, Michael Bolton, Nikka Costa, Gavin DeGraw, and Monkey House.

[40][41][42][43] A frequent visitor to Kenya and Rwanda, Woodward organizes an annual benefit concert for the Cura Orphanage outside Nairobi at Jim Henson Studios.