Christopher Carson Cheek was born on September 16, 1968 in St. Louis, Missouri, into a household where the instrument was already in the room. His father, Robert Cheek, spent 37 years as a band director in Webster Groves, and Chris took up the alto saxophone at eleven. He has credited his high-school band director, Don Kinnison, with two hours of daily instruction that mixed jazz with concert repertoire and with being the first working musician he ever met. He studied at Webster University, then at the Berklee College of Music in Boston under Joe Viola, Hal Crook and Herb Pomeroy, taking a bachelor's degree in jazz performance; a master's in jazz arranging and composition from Queens College in New York followed later. His earliest recordings come from the Boston years, on bassist Stephane Furic's Soul Note albums Kishinev (1991) and The Twitter-Machine (1993), a partnership that has run intermittently ever since.

He moved to New York City in 1992 and was inside Paul Motian's Electric Bebop Band within two years. The band's Reincarnation of a Love Bird was cut live to two-track at the Power Station in June 1994 and issued by JMT, with Cheek and Chris Potter sharing the front line, Kurt Rosenwinkel and Wolfgang Muthspiel on the two guitars, Steve Swallow on bass and Don Alias on percussion. Cheek stayed for twelve years and five more records: Flight of the Blue Jay (Winter & Winter, 1997), Play Monk & Powell (1999), on which the band worked only Thelonious Monk and Bud Powell tunes, Europe (2001), Holiday for Strings (2002) and, once the group had been renamed the Paul Motian Band, Garden of Eden (ECM, recorded November 2004, released February 2006), where he also contributed the composition "Desert Dream." In parallel he co-founded the Bloomdaddies with fellow tenor player Seamus Blake, a two-tenor electric band whose first album was recorded in New York on December 16, 1995 and released by Criss Cross in 1996 under Blake's name, followed by the self-released Racer X and Mosh for Lovers (Fresh Sound New Talent, recorded January 2001).

His own catalog began in 1997 and, for its first decade, belonged almost entirely to Jordi Pujol's Barcelona label Fresh Sound New Talent. I Wish I Knew (FSNT 022) is a quartet with Rosenwinkel, bassist Chris Higgins and drummer Jorge Rossy. A Girl Named Joe (FSNT 032, 1998) doubled the front line with Mark Turner on second tenor and added Marc Johnson and Ben Monder. Vine, recorded in New York on December 20 and 21, 1999, put Brad Mehldau at the piano alongside Rosenwinkel, Matt Penman and Rossy. Two live records, Guilty and Lazy Afternoon, came out of the same four nights at the Jamboree in Barcelona, March 21 to 24, 2000, with Ethan Iverson, Ben Street and Rossy. Blues Cruise, cut at Avatar Studios on March 16 and 17, 2005 with Mehldau, Larry Grenadier and Rossy, closed the sequence. Rossy is on every one of those records and on eleven titles in this discography, which makes him Cheek's longest-running musical relationship by a distance.

Alongside the leader dates he built one of the broadest section-player resumes of his generation, and it runs through some of the most demanding large ensembles in New York. He has held a tenor chair in Guillermo Klein's Los Guachos on five albums from Los Guachos II (Sunnyside, 1999) to Cristal (2019). He was in both incarnations of Charlie Haden's Liberation Music Orchestra under Carla Bley's direction, on Not in Our Name (Verve, recorded in Rome in July 2004) and the posthumous Time/Life (Impulse!, 2016), alongside Steve Cardenas and Matt Wilson. He is the tenor voice of Steve Swallow's quintet on Into the Woodwork (XtraWATT/ECM, recorded November 2011) and Winter Songs (ECM, recorded September 2024). Two of the big bands he plays in went to the Grammys: Dafnis Prieto's, whose Back to the Sunset won Best Latin Jazz Album in February 2019 with Cheek on baritone, and Alan Ferber's, whose Jigsaw was nominated for Best Large Jazz Ensemble Album the year before. He also plays baritone in the Identities Big Band on Miguel Zenón's Identities Are Changeable (2014), and on two tracks of Mehldau's Finding Gabriel (Nonesuch, 2019). He recorded twice with Lee Konitz and Furic on ESP-Disk, and on March 31, 2009 Posi-Tone released guitarist Yotam Silberstein's Next Page, with Cheek on tenor, Sam Yahel on organ and Willie Jones III on drums.

Since 2007 he has taught at the New School in New York, and in December 2021 the Royal Conservatoire in The Hague appointed him its main-subject teacher for jazz saxophone. His recent leader work has drifted steadily away from the piano quartet. Two Criss Cross albums reunited him with Seamus Blake under the band name Reeds Ramble, Reeds Ramble (recorded April 4, 2013) and Let's Call the Whole Thing Off (recorded September 10, 2015), both with Iverson, Penman and Jochen Rueckert. Saturday Songs (Sunnyside, June 24, 2016) was recorded in the Spanish village of Estivella in July 2015 and replaced the piano with Cardenas's guitar, David Soler's pedal steel and Rossy on drums, vibraphone and marimba. The Jerome Kern Songbook (Fresh Sound, 2020) came from two days in Barcelona in September 2018. In May 2025 the audiophile label Analog Tone Factory issued Keepers of the Eastern Door, recorded on November 8 and 9, 2024 by a quartet of Cheek with Bill Frisell, Tony Scherr and Rudy Royston, the guitarist's long-standing trio; Cheek first met Frisell on a Paul Motian gig at the Knitting Factory years earlier. He wrote the record after looking at Edward S. Curtis photographs, one of which is on the sleeve, and reading Steinbeck's The Pearl, and took its title from the Mohawk role in the Haudenosaunee Confederacy.

Cheek's sound is the least aggressive thing about him: a light, slightly dry tenor tone with very little vibrato, placed far enough behind the beat that it can read as diffidence until the line resolves somewhere unexpected. That restraint is why bandleaders as different as Motian, Bley, Swallow and Guillermo Klein have used him as a section voice rather than as a soloist to be featured, and why he has held two-tenor chairs opposite players with much bigger sounds, Chris Potter in the Electric Bebop Band, Seamus Blake in the Bloomdaddies and Reeds Ramble, Tony Malaby in Chris Lightcap's Bigmouth, without ever trying to match them for volume. He grew up on 1970s St. Louis rock and country radio before he found jazz, and that shows in his writing more than in his playing: his tunes tend to be short, singable and harmonically plain on the surface, and he has said he takes his cues from guitar-based music, which is why Saturday Songs is scored for guitar, pedal steel and marimba and why Keepers of the Eastern Door is built around Bill Frisell. He is also a genuine multi-instrumentalist within the saxophone family, and the baritone work of the last decade, on the Prieto and Zenón big bands and on Finding Gabriel, is a substantial second career that his own leader records barely hint at.