Later examples include: touring and recording with guitarist Pat Metheny; writing and playing song cycles for classical singers Renée Fleming, Anne Sofie von Otter, and Ian Bostridge; composing orchestral pieces for 2009's Highway Rider; and playing electronic keyboard instruments in a duo with drummer Mark Guiliana.

Aspects of pop, rock, and classical music, including German Romanticism, have been absorbed into Mehldau's writing and playing.

[1] His adoptive family[2] was father Craig Mehldau, an ophthalmologist,[3][4] mother Annette, a homemaker, and sister Leigh Anne, who became a social worker.

[8] Up to this point he had played mostly simple pop tunes and exercises from books, but the move brought him a new piano teacher, who introduced him to classical music.

[8] This new interest lasted for a few years, but by the age of 14 he was listening more to jazz, including recordings by saxophonist John Coltrane and pianist Oscar Peterson.

[10] While at high school, he began transcribing jazz solos from recordings, to improve his listening skills and gain insights into improvisation.

[11] From the age of 15 until he graduated from high school he had a weekly gig at a local club, and performed for weddings and other parties, often with fellow Hall student Joel Frahm.

[14] After graduating, Mehldau moved to New York City in 1988 to study jazz and contemporary music at The New School,[10][13] on a partial scholarship.

His performances with saxophonist Perico Sambeat included a tour of Europe early in 1993,[20] and Mehldau's first released recordings as co-leader, from a May concert in Barcelona.

[34][35] Mehldau's contributions to film music continued in 1997, with an accompanist role for some of the tracks recorded for Midnight in the Garden of Good and Evil.

[37] The title again attracted attention, as concert recordings from the same club had been issued by some of the biggest names in jazz, including Evans, and saxophonists Coltrane and Sonny Rollins.

[38] The studio album Songs: The Art of the Trio Volume Three followed later in 1998, and contained Mehldau originals, standards, plus Nick Drake's "River Man", and Radiohead's "Exit Music (For a Film)".

[44] Also in 1998, the pianist reunited with Redman for the saxophonist's Timeless Tales (For Changing Times),[45] and played on country artist Willie Nelson's Teatro.

[29] On the album, in addition to Mehldau's usual trio, rock musicians and instruments associated more with classical music were employed, as were experiments with prepared piano and "multiple layers of electronically enhanced sound".

[59] This, in the view of critic Ray Comiskey, did not radically change the trio's sound, but it did give them "a harder edge and pushed Mehldau more, with bassist Larry Grenadier left more in a fulcrum role, the centre around which piano and drums cavort.

[12][65] This association was based on a commission from Carnegie Hall;[12] their 2006 recording contained music set to poems by Rainer Maria Rilke and Louise Bogan.

[68] Mehldau asserted that his third solo recording "is the beginning of a freer approach, [...] and maybe [contains] more ease and fluidity in a musical texture with several simultaneous voices".

In 2009 Mehldau began a two-year period as curator of London's Wigmore Hall jazz series, which included a performance with von Otter in the second year.

[8] Again based compositionally on the theme of travel or a journey, the album was produced by Brion, and, in critic Mike Hobart's description, "probes the confluence of the arbitrary and non-arbitrary in music, of balancing what is committed to the page with improvisation.

[77] DownBeat reviewer Jim Macnie commented that, on the former album, "More than ever, Mehldau uses his instrument as a drum, popping staccato notes into the maw of the rhythm section's formidable bustle.

[32] One piece from their album, Modern Music, featured the pianists playing a composed left-hand part while improvising with the other hand; "to do both at once is a real test.

[89] Also in 2016, Mehldau and Guiliana formed a trio with guitarist John Scofield; they played in the United States before touring Europe.

[98] Mehldau cites pianists Larry Goldings (for "his full approach to the instrument") and Hays (for adding alternative harmonies to the set one), as well as guitarist Bernstein (for showing the value of playing melodic phrases instead of just rehearsed patterns) as direct influences on his own playing, in addition to David Sánchez (for rhythmic feel[99]), Jesse Davis, Kurt Rosenwinkel, Mark Turner, and the other members of his own trio.

[100] In a 2003 interview he commented on romanticism and nostalgia, linking pleasure and pain to musical expression:I love the part of the Orpheus myth where he is allowed to take his wife out of Hades on the condition that he doesn't look back at her for the trip on the river Styx.

[6]In Stuart Nicholson's words, "Mehldau's art is not based on negotiating his way through a harmonic sequence with a string of bravura licks [...] Instead he patiently weaves melodic developments from motifs, fragments and inversions of the [...] songs he plays into the fabric of his extemporizations, making the tunes gradually assume the proportions of an alternative composition.

"[101] Fordham stated that "Mehldau demonstrates immense attention to detail, control of dynamics, and patience in developing an improvisation's shape over a longer span than the chorus-structure of a popular song.

"[6] These struggles to find satisfactory endings stem from the tension between needing to close a piece and his desire to leave a sense of open-endedness – "an escape duct of possibility".

[107] As of 2010, he divided his non-touring time between living in Amsterdam and New York City;[108] this remained the case until he let the lease on the Upper West Side property lapse during the COVID-19 lockdowns.

[109] Mehldau's trio was, in Hobart's words, "the first successfully to add post-Beatles pop into the jazz repertoire without trivialising either",[8] and shifted the "traditional emphasis on bravura technique and group dynamics [...] to a focus on subtleties of touch and where-my-fancy-takes-me musings.

[110] Further influences on pianists are his "bittersweet left-hand melodies, clusters of dense mid-range chords and ability to conjoin the angularity of [Thelonious] Monk with classical romance".