Miguel Zenón joins me on The Playful Musician. Born and raised in San Juan, Puerto Rico and living in New York City Miguel is a Grammy Winner, Guggenheim and MacArthur Fellow, and a Doris Duke Artist.

Growing up in San Juan, Miguel Zenón originally thought he would study engineering, but during his senior year of high school he was drawn to jazz, much to his family’s surprise. With no musicians in his family, the transition was stressful, and he describes it as a leap of faith. Today Miguel is a Grammy-winning saxophonist, composer, and educator, recognized as a true alto saxophone legend. He is releasing his eighteenth album, and his first live recording, Vanguardia Subterránea: Live at The Village Vanguard.

Described as “one of the most esteemed and singular-voiced alto saxophonists in jazz,” it is an honor to interview Miguel. We discuss his Tiny Desk Concert, his path from classical to jazz saxophone and back again, the culture shock of leaving Puerto Rico to study at the Berklee College of Music, and how he has kept his quartet together creating music for more than 20 years.

His new album, released the same day this podcast airs, captures what it feels like to perform on the sacred ground of the Village Vanguard. It is more than a tribute to the Vanguard. It honors the foundation of music itself, the people who paved the way for Miguel to be where he is today, and the groundwork he is now laying for those who will follow.

Filipino-American saxophonist and composer Jon Irabagon joins the ranks of legendary saxophonists sharing their stories on The Playful Musician. Born in Chicago, Irabagon studied at DePaul University before moving to New York City to earn his master’s degree at the Manhattan School of Music, followed by postgraduate studies at Juilliard. He has taught on four continents and is currently on the faculty at the University of Illinois Chicago, where he teaches jazz saxophone, directs combos, and leads courses in jazz history.

Jon’s story begins in the Windy City, a place that shaped and molded his unique, evolving expression on the alto saxophone. His parents had emigrated from the Philippines in search of a place where they could find work, start a family, and feel accepted in a new country. Irabagon’s sweeping career is like hearing the American Dream set to the brassy, warm tones of the alto sax.

With his newest album, Someone to Someone, from his label Irabbagast Records debuting today August 15 we sit down to discuss how he went from being a little kid too small to carry a saxophone to the bus stop to become one of Time Out’s “25 Essential New York City Jazz Icons” and one of my personal favorite alto sax players.

In this episode, we discuss why he started his own label and his theory on releasing albums authentically, his insights from private lessons with Dick Oatts and Dave Liebman, his teaching philosophies and techniques (covering everything from goal setting to social media), how he landed a gig with Billy Joel simply by asking the right question, and his dream of one day releasing an album featuring all nine saxophones he owns and plays.

Jon’s passion for music and his ability to cut straight to the heart of what it means to be a working musician will leave you inspired and ready to stream his music.

Lafayette Gilchrist is a keyboardist, composer, and the newest piano chair in the legendary Sun Ra Arkestra.

In this episode, Gilchrist shares his story of growing up in Washington, DC, and what led him at age 17 to finally sit down at a piano and begin teaching himself to play and compose. He describes how his early love of hip-hop, funk, and go-go evolved into a passion for jazz, sparked by Chuck Brown’s riffs and inflections woven into the popular music of the time. After earning a degree in economics, Gilchrist left college to begin his professional life but also launched his band, spending hours in music stores selecting jazz albums purely by their cover art.

His is a story of individualism and discovery, a reminder that there is no single path to virtuosity or success in music. Like many professional musicians, he understands the many roles required to build a career and his journey offers inspiration to musicians of all ages.