McCaslin's father originally taught high school English but favored being a jazz musician, playing the vibraphone and piano at local gigs with young McCaslin in the audience. When he was 12 years old, McCaslin joined his father's group. By the time he was in high school he had formed his own band, and was selected to play at the Monterey Jazz Festival for three years in a row. During high school he also performed with an eight-piece salsa band, and spent much time at the Kuumbwa Jazz Center, where nationally known jazz artists gathered. He studied with Paul Contos and Brad Hecht, accomplished members of his father's groups, and was influenced by the likes of John Coltrane, Michael Brecker, and Sonny Stitt.
McCaslin's technique and expression allowed him to tour with all-star youth ensembles throughout Europe and Japan, and he won a full scholarship to Berklee College of Music starting in 1984. His main influences there included Gary Burton, Herb Pomeroy, Billy Pierce, George Garzone, and Joe Viola. During his senior year at Berklee he joined vibraphonist Burton's quintet, and for four years the group toured Europe, Japan, North America, and South America. During 1991, after moving to New York City, McCaslin became a member of Steps Ahead, and played with them for over three years. Michael Brecker, formerly of Steps Ahead, had been one of McCaslin's teenage idols; now McCaslin was replacing him. McCaslin co-wrote two of the compositions that appeared on the group's album Vibe. During those same years, McCaslin actively gigged with top jazz artists and groups, such as the Gil Evans Orchestra, George Gruntz Concert Jazz Band, the Danilo Perez Quartet, the Maria Schneider Jazz Orchestra, and Santi Debriano's Panamaniacs, plus he appeared on many recordings. In 1996, McCaslin was featured with John Medeski (organ), Doug Yates (clarinet), and Uri Caine (piano) in Ken Schaphorst's big-band work "Uprising." Three years later, Naxos Records released the piece on Purple, and the jazz media gave McCaslin's solo work rave reviews.
During 1997, McCaslin joined with David Binney (alto), Scott Colley (bass), and Kenny Wollesen (drums) to form Lan Xang, an experimental jazz collective that released Mythology. The name Lan Xang symbolizes freedom, the bandmembers' concept of experimental jazz. In 2000, Lan Xang released Hidden Gardens and they continued to play gigs together, presenting unique forays in group improvisation. In 1998, Naxos released Exile and Discovery, McCaslin's first solo record. Playing with him were Ugonna Okegwo (bass), Bruce Barth (piano), and Billy Drummond (drums). Arabesque Records released 2000's Seen from Above, an album in which McCaslin integrates blues, swing, and fusion, reflecting his skill both as a composer and a soloist. Way Through, released by Arabesque in September 2003, was his third solo album.
His skill was celebrated by critics, musicians, and fans alike, enhancing his reputation as a leader and valued sideman. He briefly joined the Dave Douglas Quintet in 2006, and recorded two albums on his own that year for two different labels: Give and Go (CrissCross) and Soar (Sunnyside). For the latter he also recorded In Pursuit a year later and appeared on the Maria Schneider Jazz Orchestra's Sky Blue (and received one of his three Grammy nominations for a solo he performed). McCaslin made his debut for Greenleaf in 2008 with the trio album Recommended Tools, produced by Binney. The following year he received second billing on Now What by Julie Lamontagne, and was a featured participant on albums by vocalist Monday Michiru and guitarist Paul Myers.
The saxophonist spent most of 2010 touring and playing club gigs. In 2011, he released the eclectic septet date Perpetual Motion on Greenleaf Music. Its lineup included old friends, bassist Tim Lefevbre and drummer Mark Guiliana, who would soon make up half of his working quartet. Pianist/keyboardist Jason Lindner would come aboard for their first proper date together, Casting for Gravity in 2012. McCaslin received a Grammy nod for best jazz solo for it as well. His band did a lot of road and club work for the next couple of years, including a regular run at 55 Club in Greenwich Village. They also worked in the studio.
In 2014, the saxophonist was part of the Maria Schneider Orchestra that backed David Bowie on his single "Sue (Or in a Season of Crime)." The singer then approached the pianist about working on his next album. Since she was tied up with her own massive project, she suggested he check out McCaslin's band at 55 Club. The singer (already ill) did and invited the quartet to record. They worked monthly from January through March 2015 in three week-long sessions. The saxophonist's Fast Future -- the product of the previous year's sessions -- also appeared in March from Greenleaf. Bowie's Blackstar, featuring McCaslin's quartet, guitarist Ben Monder, and several others, was released on January 8, 2016 to massive acclaim. Bowie died two days later on his 69th birthday. McCaslin and his band, who were among his final collaborators, were deeply moved by the music they'd worked on together. The saxophonist began creating a new album for the band in tribute to the singer. He had signed to Motema the year before, and in the late spring his quartet entered a recording studio. They emerged with the full-length Beyond Now; it included covers of tunes by Deadmau5, MUTEMATH, the Chainsmokers, as well Bowie's "A Small Plot of Land" (with Jeff Taylor on vocals) and "Warsawa" -- its first two singles -- and was released in October. After a spate of international touring during which McCaslin felt he'd completely absorbed the influence and inspiration of Blackstar in his own work, he began writing and cutting demos that expanded the connecting points found on Beyond Now. In 2017 he began pre-production on an album with Steve Wall, and began tying together the kaleidoscopic soundworlds he'd been exploring with Bowie and his own group in the aftermath of the singer's passing. Vocals played a large part in the creation of the work he was recording. McCaslin recruited the talents of Sun Kil Moon's Mark Kozelek, Gayle Ann Dorsey, Ryan Dahle, and Jeff Taylor, to front his band, which included Jason Lindner on keyboards, Tim Lefebvre on electric bass, and Mark Guiliana and Zach Danziger on drums and programming. Two advance singles, "Great Destroyer" and "Club Kidd," showcased McCaslin's fascination with avant pop. The finished album, entitled Blow. was issued in September of 2018 on Motema. ~ Eleanor Ditzel, Rovi