David Kikoski learned the instrument at home. His father taught him piano in Milltown, New Jersey, and the two of them worked bars together while the son was still a teenager, which is an unglamorous apprenticeship and a thorough one. He went to Berklee in the early 1980s and moved to New York in 1985, and the gigs arrived almost at once. By 1986 he was in Roy Haynes's band, a job he would still be doing decades later and the single most important relationship of his career. The first document of it is True or False, cut at the Magnetic Terrace in Paris on October 30, 1986 for the French label Free Lance, a quartet with Ralph Moore on tenor and Ed Howard on bass. Within a year he was also on Ralph Moore's 623 C Street (Criss Cross, 1987) with Buster Williams and Billy Hart, and on Randy Brecker's In the Idiom (Denon, 1987) in a band with Joe Henderson, Ron Carter and Al Foster. He toured with Brecker from 1986 to 1988, joined Bob Berg's electric group in 1988 for Cycles (Denon), recorded at Skyline Studios that June alongside Mike Stern and Dennis Chambers, and began working with Billy Hart in 1989.

His own first record came out of the same French connection. Presage was cut in New York on July 31 and August 1, 1989 with Eddie Gomez and Al Foster and issued by Free Lance, and it set a pattern he has kept to: a trio, standards mixed with his own writing, no concept beyond playing. Persistent Dreams (Triloka, recorded October 17 and 18, 1991 at Clinton Recording Studios) is the outlier in the catalog, an eleven-piece production with flute, guitar, percussion, a vocalist and Randy Brecker's trumpet, produced by Walter Becker of Steely Dan. Three years later Epic gave him a major-label date, Dave Kikoski (1994), recorded at the Power Station as a trio with Essiet Essiet and Al Foster. It remains his only album for a major, and the shape of his career after it is the shape of an independent-label musician.

The Haynes association kept generating records through the 1990s: When It's Haynes It Roars!, taped at Davout Studios in Paris on July 25 and 26, 1992; Homecoming, a live WGBH broadcast from Boston on June 27, 1992; Te Vou! in 1994 with Pat Metheny, Donald Harrison and Christian McBride; and Praise, cut at Systems Two in Brooklyn over three days in May 1998 with Kenny Garrett and David Sanchez. In the same stretch Kikoski joined the Mingus Big Band, where he has now spent close to thirty years, first at the band's Monday-night residency at the Jazz Standard and later on Tuesdays at the Django. He appears on Que Viva Mingus! (1997), Blues & Politics (1999), Tonight at Noon (2002), Live in Tokyo (2006), Live at Jazz Standard (2010), Mingus Sings (2015) and both volumes of The Charles Mingus Centennial Sessions (2022 and 2024). He also co-produced and co-arranged Bob Berg's Another Standard (Stretch, 1997), a record Chick Corea executive-produced, which is the clearest documentation of Kikoski working as something other than a hired pianist.

The body of his leader work belongs to Criss Cross Jazz and to its founder Gerry Teekens, who recorded him ten times between 1997 and 2016, almost always at Systems Two in Brooklyn with Max Bolleman engineering. The run goes Inner Trust (December 19, 1997, with Ed Howard and Leon Parker), The Maze (June 8, 1998, adding Seamus Blake and Scott Colley), Almost Twilight (December 11, 1999, with John Patitucci), Surf's Up (January 18, 2001, with James Genus), Combinations (December 16, 2001), Details (December 18, 2003, with Larry Grenadier and Bill Stewart), Limits (December 7, 2005), Mostly Standards (June 18, 2008, with Eric Revis), Consequences (February 1, 2012, with Christian McBride) and Kayemode (September 20, 2016, with Joe Martin and Justin Faulkner). Jeff "Tain" Watts is the drummer on seven of those ten, which makes him Kikoski's closest and longest-running partner. In between, on consecutive days in Tokyo in August 2001, he made two albums for the Japanese label DIW: the quintet date The Five on the 27th with Alex Sipiagin and Blake, and the trio record Comfortable Strange on the 28th.

The awards came from other people's bands. Birds of a Feather: A Tribute to Charlie Parker, recorded March 26 and 27, 2001 by Roy Haynes with Kenny Garrett, Roy Hargrove, Dave Holland and Kikoski, was nominated for Best Jazz Instrumental Album at the 44th Grammy Awards. Ten years later the Mingus Big Band's Live at Jazz Standard, taped at the club on New Year's Eve 2008 into 2009 and released in 2010, won Best Large Jazz Ensemble Album at the 53rd Grammy Awards on February 13, 2011, making Kikoski a Grammy winner as well as a nominee. The band was nominated again for The Charles Mingus Centennial Sessions.

Two collective bands account for a large share of his recent output. BeatleJazz, co-led with drummer Brian Melvin and originally with bassist Charles Fambrough, reworked Lennon and McCartney tunes across four albums between 2000 and 2007, starting with A Bite of the Apple, taped in New York in November 1998 and issued by Zebra Acoustic, and reconvened in 2025 for Reunion. Opus 5, a genuine cooperative with Sipiagin, Blake, Boris Kozlov and Donald Edwards, made five records for Criss Cross between the January 27, 2011 debut and Swing On This, recorded September 7, 2021. His own leader work moved to HighNote for Phoenix Rising, cut at Van Gelder Recording Studio on December 20, 2018 with Eric Alexander, Peter Washington and Joe Farnsworth, and Sure Thing, a bass-and-piano duo with Kozlov recorded in Brooklyn on February 3, 2016 and held back until 2021. In October 2020 he spent a day at Big Orange Sheep Studios in Brooklyn recording three standards in duo with guitarist Peter Bernstein, one of four such duo sessions that the French label Diggers Factory gathered into the 2xLP The Complete Orange Hours. His most recent album, Weekend at Smalls, was recorded at the Greenwich Village club on September 9, 2024 with Joe Martin, Billy Hart and Randy Brecker and released by Cellar Music on September 26, 2025.

Kikoski is a rhythm player first. What his bandleaders keep describing is not a harmonic signature but a way of sitting in time: Roy Haynes, the most demanding rhythmic judge in the music, kept him in the band for over thirty years, and Chick Corea called his playing sparkling. The vocabulary is post-bop, dense and fast, but the temperament is closer to the Blue Note hard-bop pianists: he would rather swing a standard than open it out. The evidence for this is in the record titles as much as the records. Mostly Standards, Inner Trust, Details, Sure Thing and Weekend at Smalls are all trio or quartet dates of familiar material played hard, and Persistent Dreams, the one album that reached for a bigger production, was never repeated. The range is wider than that suggests, though, and it shows up on other people's sessions rather than his own: he plays synthesizer on Bob Berg's electric bands, Fender Rhodes with Opus 5 and Eddie Henderson, and a full keyboard rig on Randy Brecker's Soul Bop group and Bill Evans's country-jazz project Soulgrass, without ever making an electric record of his own. Critically he has been treated as a musician's musician rather than a headliner, which the Grammy history bears out: the win and the nominations all belong to records led by other people.