Alex Leong

Alex Leong is a student of music.

In addition to holding a bachelor of music degree in commercial music from Millikin University in Decatur, Illinois, Leong also is a former music librarian at Madison Area Technical College; a supervisor for music curation, live audio production and DJ services for public concerts and private events, and the creator of a website that includes more than 200 free transcriptions, song biographies and curated playlists.

But the 2000 Milton High School grad and self-proclaimed “music nerd” is at his best on stage, wielding his trombone for the likes of Chicago’s famed Four Star Brass Band, Nashville songwriter Mike Maimone and James Brown’s famous “Funky Drummer,” the late Clyde Stubblefield.

“My real education came directly from gigging,” Leong said. “My experience playing with Clyde Stubblefield taught me the mechanics of playing within a band, establishing the groove and hosting an audience.”

Leong confides he doesn’t perform for riches or personal accolades. His goal is to help cultivate a consistent “feel-good” vibe with his music.

A longtime resident of Chicago, Leong’s interests also include studying improvisational comedy at such venues as The Second City Training Center, the iO Theater and The Annoyance. He also considers himself a “deep aficionado” of close-up magic and professional wrestling.

Leong’s family include his parents, Wilson and Kathy of Milton, and a brother, Eric, who lives in Madison with his wife and two kids.

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1. What initially drew you toward the trombone? My band director, Mr. Ken DeVoe, suggested my embouchure would be more suited for the trombone rather than my first choice, the trumpet. I didn’t mind because my best friend also played the trombone, but in hindsight, I suspect Mr. DeVoe just needed more trombones in the band.

2. Do you play any others instruments? I play keyboards in “Don’t Speak: A No Doubt Tribute,” I dabble on guitar and ukulele, I’ve been DJ-ing more during the pandemic, and on a good night you might find me at the karaoke bar. I’d still like to be a competent bassist and/or drummer, and I’m looking to acquire a sousaphone so I can lead my own brass band someday.

3. Do you model your playing style after another musician, or do you try to do your own thing? My primary influences have been Fred Wesley and New Orleans brass bands, but more recently, I’ve focused on the Caribbean styles of Don Drummond and Mon Rivera. I’m not trying to break any new ground, I just want my sound to reflect those influences and to resonate with my audience.

4. You recently worked with Nashville singer/songwriter Mike Maimone on his new album “Broke, Not Broken.” Was that your first time doing album work? I recorded with Mike in 2017 for “The High Hat Club” EP, named after a now-defunct bar in Chicago where we all first met. It was the kind of place where if you show up early in the night you can still catch the end of last night’s party, and I feel like the EP captured that spirit. I’ve also recorded with blues singer Liz Mandeville, indie rocker William Steffey and probably on some other uncredited releases.

5. How and when did you discover music was your passion? I’ve been fortunate enough to have access to decent music education programs, so it’s always been an outlet for self-expression and therapy. But when I first saw Youngblood Brass Band play at Milwaukee’s Summerfest in 2000, and then learned about the traditions of New Orleans music, that was it.

6. How many types of trombone are there, and what are the differences between them? The most common is the tenor slide trombone. In an orchestra, you might also see a larger bass trombone and a comically-small alto trombone. Some styles of jazz and Latin music will feature a tenor trombone with valves, like a trumpet, instead of the moving slide. Also, carbon fiber and plastic trombones have become popular in recent years.

7. Do you perform full-time? Performing typically doesn’t pay the bills, by itself. Prior to the pandemic, I performed regularly with three or four groups, I’d sit in with other bands as a substitute, and I worked as a wedding DJ. I get paid for recording sessions, I collect fractions-of-a-cent on Spotify, and I occasionally get commissioned to write music. I also have a Patreon account where fans contribute a few bucks each month to help cover the costs of freelancing as an independent musician. On top of all of that, I’ve worked a dozen or so odd jobs and seasonal office positions to help fund my music career, or at least my half of monthly rent.

8. What type of music did your parents listen to when you were a child? Did it influence your future tastes? I remember a lot of Neil Diamond, drum and bugle corps, Andrew Lloyd Webber, doo-wop, Motown, and Paul Simon’s Graceland. I have a vivid memory of listening to a scratched vinyl copy of The Beach Boys’ Pet Sounds that had the scariest skipping loop during the song “Wouldn’t It Be Nice.” I’m sure none of that had any influence whatsoever on my “Weird Al” Yankovic phase.

9. Name a skill you wish you had. Are you aware of how kids multiply numbers these days?!

10. Do you play video games? If so, what kind? If not, what would you say is your most enjoyable “time waster”? I prefer the classic arcade and social games. There’s a bar in Kalamazoo, Michigan, called The Beer Exchange where the menu prices change in real-time based on the “market value,” and they have a pinball machine on which a friend taught me the actual strategy for keeping the silver ball alive. I dare you to find me a better “time waster” than that night in Kalamazoo.

11. You performed regularly with the original funky drummer, Clyde Stubblefield. How did that opportunity come about, and describe your working relationship. I heard from a friend that Clyde had been looking for horn players for his weekly gig in Madison, so after a show one week I got the courage to introduce myself and Clyde told me to bring my horn the next week, and then the next week, and the week after that and so on, until he started calling me for other gigs. I played in his band for three years. It was the best education I’ve ever received.

12. You’ve performed with blues, funk, ska, New Orleans jazz acts and more. Is there a particular style you enjoy more than the others, or does the diversity keep you challenged? Music is music, and all music is good. The benefit of learning different musical styles is that it forces you to view your own playing from another perspective, and the goal for any musician should be to sound like their most authentic self.

13. You were once a guest lecturer at your alma mater, Millikin University. What did it feel like to be asked back to speak to students after having been a student there yourself? Have you ever had that nightmare of forgetting to turn in an assignment for your final grade? It felt like that and having to give the ultimate senior presentation, or “What I Did On My 10-Year Summer Vacation.” But it was also a dream come true, and I hope to get to do it again.

14. You are the creator of, an educational resource that offers free transcriptions, song bios and curated playlists. How did the idea for that come about, and how are you able to keep it going? My friend, a Nashville guitarist, started a blog where he posted his guitar transcriptions as an excuse to practice transcribing. I wanted to learn how to play New Orleans music, so I followed his model and started figuring it out for myself. But there’s no substitute for actually learning music in New Orleans through the aural traditions.

15. What is the coolest thing to happen to you? When I think about it, the single coolest thing that has ever happened to me is: I’ve been lucky and privileged throughout my career to be in the right place at the right time, but the most meaningful experience has been playing brass band music in Chicago for New Orleans natives who had been displaced due to Hurricane Katrina, and hearing from them, “You make me feel at home!”

16. What is the one thing that goes into your cart at the grocery store whether you need it or not? Ben & Jerry’s Phish Food.

17. You’ve played some big shows in front of a lot of people. Do you, or have you, ever been nervous about going out on stage? All the nerves about crowd size disappear the moment when complete trust has been established onstage within the band. That’s what I learned from taking improv comedy classes in Chicago, where you’re taught to trust and support your scene partners, and that “the worst thing that can happen” is that the audience will laugh at you—which is the primary job of being an entertainer.

18. You define yourself as a “music nerd?” How does one attain such a prestigious title? The formal title would be “musicologist” or an academic who studies the cultural and historical significance of music, but I prefer having such record-store discourse as: Under which letter would you file the stage name “Iggy Pop?” The correct answer is “S” for The Stooges, of course.

19. Do you have any superstitions? Every morning, I listen to Stevie Wonder, Muddy Waters, Eddie Floyd and Albert King’s greatest hits … or else!

20. If you weren’t a musician, what would you be doing now? I don’t have an answer to this because EVERYTHING is music—a daily routine is a rhythm, every sound is a melody, and communication is harmony. When I trained for the Chicago Marathon, I ran without headphones because there’s always music playing in my head and it kept me motivated over the long distances. Music is what gets me through the toughest parts of life.

EDITOR’S NOTE: “20Q” is a regular feature of Kicks, the arts and entertainment section appearing in every Wednesday edition of the Janesville Gazette. Former Milton resident Alex Leong answered Kicks editor Greg Little’s 20Qs for this feature that originally appeared in Kicks earlier this month.

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