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In 2017, under the group name Masakowski Family, they released the album N.O. Escape, a combination of electric jazz, gypsy jazz, and vocal jazz. Steve Masakowski co-wrote three songs that were based on the novel A Confederacy of Dunces.

He has been voted Best Guitarist twice and included as a member of Astral Project in the Best Contemporary Jazz Group three times by Gambit and Offbeat magazines in their annual readers' poll. He has published lessons in Guitar Player magazine and wrote the book Jazz Ear Training – Learning to Hear Your Way Through Music for Mel Bay Publications. He has also been recognized by Down Beat magazine as Guitar Talent Deserving Wider Recognition.

He was hired by Marsalis to teach in the jazz program at the University of New Orleans. In 1991, he became a full-time faculty member. After the retirement of Marsalis and a short tenure by Terence Blanchard, he became Chair of Jazz Studies and director of the jazz program in 2004.

He has released solo albums and has worked with Johnny Adams, Mose Allison, Dave Liebman, Ellis Marsalis, Jr., Carl Fontana, Rick Margitza, Bobby McFerrin, Nicholas Payton, Dianne Reeves, Sam Rivers, Woody Shaw, Alvin Tyler, and Bennie Wallace. Since 1987, he has been a member of the band Astral Project.

For three years, Masakowski worked in a duet with pianist Ellis Marsalis, Jr. In 1987, he joined Astral Project. From 1993–1996, he toured with singer Dianne Reeves. He leads the band Nova NOLA, whose members include his son, double bassist Martin, and his daughter, vocalist Sasha Masakowski. He released two albums for Blue Note Records: What It Was (1994) and Direct AXEcess (1995). New Orleans guitarist, banjoist, and historian Danny Barker wrote the liner notes for What It Was. When Barker died in 1994, he bequeathed his acoustic guitar to Masakowski.

In 1987, Masakowski invented the switch pick to help when switching from fingers to plectrum. "I invented something I call a switch-pick, which is a sort of thumb pick...[made] in such a way that if I slide it up my finger, the support part doesn't come in contact with my thumb, so it feels like a normal pick. And then if I want to use it as a thumb pick, I just slide it up my finger, and I can play finger style with the thumb pick using all five fingers."

In 1982, Masakowski founded the Composers Recording Studio with harpist Patrice Fisher, guitarist Jimmy Robinson, and violinist Denise Villere. He often acted as audio engineer and sometimes record producer. The studio lasted about ten years and recorded Harry Connick Jr., Ellis Marsalis Jr., Tony Dagradi, the Dirty Dozen Brass Band, and pianist James Drew.

In 1982, Masakowski married German pianist Ulrike Antonie Sprenger. The couple have two children, both professional musicians: vocalist Sasha Masakowski (b. 1986) and double bassist Martin (b. 1990). Since 2007, the Masakowski family has been playing in bands together, including the group Nova NOLA.

In the early 1980s, Masakowski played regularly with local New Orleans musicians such as Earl Turbinton, Jr., Alvin Tyler, and Willie Tee. With Singleton and drummer Johnny Vidacovich, he accompanied visiting musicians such as Randy Brecker, Tom Harrell, Art Baron, and Dave Liebman. He founded the group Mars with Larry Sieberth (keyboards), James Singleton (bass), and James Black (drums). The band played a mixture of jazz and electronic music, sometimes combined with visual art created by Jon Graubarth. Dave Liebman played on the first Mars album (1983).

In 1978, Masakowski invented the key-tar, a guitar-like instrument with seven rows of keys instead of strings, one key at each fret. This pre-MIDI controller was hardwired to a Moog synthesizer. One advantage of such an instrument was that it allowed playing more than one note in a row of keys at the same time, the equivalent on the guitar of playing multiple simultaneous notes on one string. Masakowski's song "Stepping Stone" was composed on the keytar, which allowed for the cluster-type chord voicings. For the duration of the Mars era, his rig included a Gretsch seven-string guitar with the keytar fastened to the top. He chose not to pursue a patent for the keytar, opting to concentrate on a revised prototype of the instrument that failed due to lack of funding.

He went to the Berklee College of Music in 1974, studying music theory, arranging, and composition. After getting his degree, he returned to New Orleans with his girlfriend, jazz guitarist Emily Remler, and founded the group Fourplay (not to be confused with the later jazz group of the same name). From 1976 to 1978, he studied classical composition and orchestration with Bert Braud, a teacher at the New Orleans Center for Creative Arts who also taught Terence Blanchard, Harry Connick, Jr., Branford Marsalis, and Wynton Marsalis.

Steve Masakowski (born September 2, 1954) is jazz guitarist, educator, and inventor. He did not invent the guitar-based keytar but did invent the switch pick and has designed three, custom-built seven-string guitars. He developed an approach to playing the guitar by using his pick design, allowing him to switch from fingerpicking to flatpicking.

Masakowski was born in New Orleans, Louisiana, on September 2, 1954. The Beatles influenced his desire to play guitar. When he was fourteen, he played bass guitar and co-founded the band Truth, which was based on the rock band Cream. In high school he became interested in composing, and he started taking guitar lessons to learn about harmony. His teacher introduced him to the music of jazz guitarists Joe Pass, Wes Montgomery, Pat Martino, and Lenny Breau.