Ndegeocello honed her skills on the D.C.
go-go circuit in the late 1980s with the bands Prophecy, Little Benny and the Masters, and
Rare Essence. Going solo, she was one of the first artists to sign with
Maverick Records, where she released her debut album,
Plantation Lullabies. This recording presented a distinctly
androgynous persona. Her biggest hit is a
duet with
John Mellencamp, a
cover version of
Van Morrison's "
Wild Night", which reached No. 3 on the
Billboard charts. Her only other
Billboard Hot 100 appearance has been her self-penned "
If That's Your Boyfriend (He Wasn't Last Night)", which peaked at No. 73 in 1994. Also in 1994, Ndegeocello collaborated with
Herbie Hancock on "Nocturnal Sunshine," a track for the
Red Hot Organization's compilation album,
Stolen Moments: Red Hot + Cool. The album, meant to raise awareness and funds in support of the AIDS epidemic in relation to the African American community, was heralded as "Album of the Year" by
Time magazine. She had a No. 1 dance hit in 1996 with a
Bill Withers cover song called "
Who Is He (And What Is He to You)?" (briefly featured in the film
Jerry Maguire) as well as Dance Top 20 hits with "Earth", "
Leviticus: Faggot", "Stay" and the aforementioned "If That's Your Boyfriend.. Last Night)". Ndegeocello played bass on the song "I'd Rather be Your Lover" for
Madonna on her album
Bedtime Stories. Ndegeocello was also tapped, at the last minute, to perform spoken word on the same song. This came after Madonna and producers decided to remove
Tupac Shakur's rap (which he did while he and Madonna were dating in 1994), after he had criminal charges filed against him. Ndegeocello also performed spoken word on
Chaka Khan's single "
Never Miss the Water", from the album
Epiphany: The Best of Chaka Khan, Vol. 1, released in 1996. The song reached No. 1 on Billboard's Dance Club Play Chart and No. 36 on the Hot R&B/Hip-Hop Singles Chart. Her music has been featured in a number of film soundtracks including
How Stella Got Her Groove Back,
Lost & Delirious,
Batman & Robin,
Love Jones,
Love & Basketball,
Talk to Me, ''
Tyler Perry's Daddy's Little Girls, The Best Man, Higher Learning, Down in the Delta, The Hurricane, Noah's Arc: Jumping the Broom, Soul Men, and Biker Boyz''. She has appeared on recordings by
Basement Jaxx,
Indigo Girls,
Scritti Politti, and
The Blind Boys of Alabama. On
The Rolling Stones' 1997 album
Bridges to Babylon she plays bass on the song "
Saint of Me". On
Alanis Morissette's 2002 album
Under Rug Swept, she plays bass on the songs "
So Unsexy" and "You Owe Me Nothing in Return". Also that year, she appeared on
Gov’t Mule’s record
The Deep End, Volume 2, playing on a cover of The
Staple Singers’ song "Hammer and Nails". And in 2009, she appeared on
Zap Mama's album
ReCreation, playing bass on the song "African Diamond". She can also be seen in the documentary
Standing in the Shadows of Motown, singing
The Miracles' "
You've Really Got a Hold on Me" and
The Temptations' "
Cloud Nine". In the late 1990s, she toured with
Lilith Fair. She also did a remake of the song "
Two Doors Down" on the 2003 release ''
Just Because I'm a Woman: Songs of Dolly Parton''. Ndegeocello was also a judge for The 2nd, 12th, 13 and the 2015 14th Annual Independent Music Awards to support independent artists' careers. Her song "Tie One On" was chosen as the
Starbucks iTunes Pick of the Week on February 23, 2010. In 2016, she provided the theme song, "Nova", for the
Oprah Winfrey-produced show
Queen Sugar. She also collaborated with French-Cuban duo
Ibeyi in the song "Transmission/Michaelion" for the album
Ash reciting a poem by
Frida Kahlo. In December 2016, the world premiere of Ndegeocello's
Can I Get a Witness? The Gospel of James Baldwin, a new theatrical music and art work, was held in Harlem, New York. In June 2021,
The Beatles Channel on
Sirius XM Radio began broadcasting
A Shot of Rhythm and Blues: Exploring The Beatles and Black Music, a four-part series hosted by Ndegeocello. The series explores the relationship between the English rock band
the Beatles and the black musicians that inspired them. ==Activism==