Whalum began his career performing with artists such as
Al Green and
Isaac Hayes. He played saxophone and arranged horns on Jay-Z's albums
American Gangster (2007) and
4:44 (2017). He has also toured and recorded with
Maxwell,
Beyoncé,
D’Angelo,
Frank Ocean, and
Mac Miller. In 2011, Whalum performed in pianist
Kris Bowers ensemble at the Jazz Gallery in New York City. A review in
The New York Times praised the group's "ambition and phrasing" and noted Whalum's role in the ensemble's sound. In 2014, Whalum contributed to Kris Bowers’ album
Heroes + Misfits. Whalum's song "Might Not Be OK," featuring
Big K.R.I.T. drew national attention when K.R.I.T. performed its spoken-word verse at the
2016 BET Hip Hop Awards as a statement on racial injustice. In 2014, Whalum played in a
Big K.R.I.T. song called "Standby (Interlude)". In 2025, Whalum performed with the
Trey Anastasio Band. On 18th October 2025, Whalum performed alongside
Sabrina Carpenter in the songs
Nobody's Son and
Manchild during her appearance on
Saturday Night Live. == Solo work ==