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.

[1] 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.

His teacher introduced him to the music of jazz guitarists Joe Pass, Wes Montgomery, Pat Martino, and Lenny Breau.

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.

The band played a mixture of jazz and electronic music, sometimes combined with visual art created by Jon Graubarth.

In 1982, Masakowski founded the Composers Recording Studio with harpist Patrice Fisher, guitarist Jimmy Robinson, and violinist Denise Villere.

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.

He leads the band Nova NOLA, whose members include his son, double bassist Martin, and his daughter, vocalist Sasha Masakowski.

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.