Something about Sunday nights in December makes Cactus Club the perfect place to commune over great grooves and danceable beats. A growing crowd got cozy and joined Rap J & Friends at an uplifting all-ages show on Dec. 21, ideally timed to take the edge off the pre-holiday rush. Rap J is known for rhymes loaded with wisdom and humor. But before I checked out the Milwaukee star-studded event, I caught up with Rap J to talk about his new LP, his various collaborations and the magic of the Drunken Cobra.
It’s time to pick your Milwaukee favorites for the year!
Interview with Rap J: True Stories
Milwaukee’s Rap J, born Jaquawn Gaston, and I spoke by phone on Thursday, Dec. 18.
I listened to your new album, LIMITLESS, and I really enjoyed it. What was the inspiration for this new release?
Thank you. One night, I was watching this cool Elvis documentary about his comeback special. He was with all of his former bandmates; I could just see all the joy and energy. To be completely honest, I wasn’t per se the biggest Elvis fan or anything like that, but I was just scrolling on a winter’s night, and it led to something really cool. The next day I woke up and thought I wanted to make something fun that felt special and unique. This project was the one I had the most collaborations with, and it all started by getting inspired by that documentary.
Who were some of the artists who got you excited back when you were a kid?
When I heard Biggie on the radio … that’s what inspired me to get into music because my family would dance, and how good it would make them feel whenever he came on the radio. MJ was a very big influence. He was the one perfect artist to me. I would listen to Jimi Hendrix, Queen – anything that felt good, I would vibe with it growing up.
Your song “Ride” has great energy. What can you tell me about that song?
Ride was inspired by a true story. Funny thing: I would go to this bar called Drunken Cobra, where I met Darrin Alston and Amara there as well. One night, it got a little wild and I wanted to pay a tribute to the Cobra. We shot the video there cuz that place has changed my life so much. It was cool to pay a tribute to the place.
What about “Medicine (feat. Riz)”? The video was fantastic and I really dug the horns at the end.
Riz used to be my teacher back in middle school. It’s been so special to share this journey with Riz. He played the horn on “Medicine.” I just wanted to make a song for those late summer nights or taking a long drive.
How about “Rock Out (feat. Betty Mauritz)?” I felt like that track should definitely be on the radio.
Thank you. I was super-duper excited about “Rock Out” because I don’t think I ever rapped at that pace before. I was really pushing myself. I’m a big fan of Gold Steps, and another dream for my album was working with Betty Mauritz.
On “Boss Lingo,” there’s a little speech at the end. What’s going on with that song?
This was dedicated to my good friend Annie. We’ve been super close, and I asked her to do the intro. Whenever we had conversations, she told me to be aware of the people who are in my circle. So, at the end of the song, she’s saying stay true to yourself and the people who support you, they’ll be there, and that’s your circle. I’ve been wanting to get her on a song for a while … I think that it turned out great.”
Anything people should know about you and what’s ahead for Rap J in 2026?
This year has been a milestone year for me. Being at Summerfest, Shank Hall and Cactus Club. It’s an honor to entertain and it’s an honor to be able to create. Every time you come to a Rap J & Friends show, you’re gonna get the best that we got. You’re gonna get a little funk, little R&B, a lot of rap. You’re gonna hear some singing. I just want to create a great environment for everyone. It’s just an honor to entertain people. Be on the lookout for the “Let’s Dance” video that’s dropping early [next] year.
Friends and Family Pack the Cactus Club
Darrin Alston kicked off the show with a raucous performance that featured humor, insightful lyrics and a shoutout “to all my geeks out there, to those attending Comic-Con” before launching into the song “Sentiments” from his new EP, Chasing Stars. Alston revealed the deepness rooted in his creations with “Ganbaru Bars,” a song connecting the Japanese proverb for doing your best/toughing it out to his own life experiences. He tore through “Awww Maaan,” a song dedicated to all the people who say they’re going to attend your show but don’t show up. Alston’s infectious energy carried the irresistible “Hit That One-Two” and provided a nice leadoff to the night’s lineup.
Amara took the stage next and changed the tempo with her piano-driven songs, delivered with cool, assured vocals in a lovely duet with singer Parker Nieves in which they harmonized about silver linings in hell. The song carried the delicate power of singer-songwriters like Fiona Apple, who Amara covered in her next tune. Amara played piano with the assured delicacy of early Tom Waits and all the pleasing minor-key surprise of Joni. Looking forward to hearing more from this up-and-coming Milwaukee singer and pianist.
Riz entered the equation with star power times two, dark shades on and catchy as hell hooks punctuated with irresistible dance moves. Starting and ending his set with a song about a dance floor encounter with a more experienced partner, Riz also shared his Rap J origin story: “This guy rolled in my classroom all those years ago, freestyling in my classroom 40 minutes a day. I was teaching him, but I’ve spent the last few years learning from him. I’m talking ‘bout Rap J.”
Riz rocked into his next song with some Prince-ly vocalizations (and late-night lowdown body moving), with smooth jam dance floor-ready beats kept steady by DJ Dscribe, whose well-timed quips and cracks kept the crowd loose.
Warming up for Rap J to take the stage, Darrin Alston reminded the crowd to support local artists, including themselves. He encouraged everyone to frequent clubs like Drunken Cobra because “karaoke is the secret networking” among aspiring musicians, singers and rappers in Milwaukee.
Headliner Rap J gave a quick message of gratitude before his set began: “This is an early Christmas present for me, to be playing Cactus Club in front of all you people … the most important thing we can share together is our time and love.” He gave a humorous intro to “Rock Out,” punctuated by a shoutout to a friend “for being super strong and super fast … pushing me, literally, to make the bus. She’s a hero.” (Rap J uses a wheelchair due to cerebral palsy.)
Again, DJ Dscribe kept the mood light with hilarious interjections. A running gag involving the word “allegedly” added more spice to the between-song banter, making the friends and family affair feel right at home. For example, Rap J claimed he could “allegedly” be doing donuts at Humboldt Park after the show.
Rap J opened the song “Don’t Sleep Me” with a reminder to the audience: “Some people wanna sleep on you, this song is to wake ’em up.” Everyone at Cactus Club was wide awake on this December Sunday night, thanks to great beats, fluid raps and the incredible chemistry between the artists.
Finally, after delivering a few more silky grooves from his 2025 release, Limitless, Rap J closed the show with another humble nod to what he said has been the best year of his life – and another ribbing.
In keeping with the friends-and-family feel of the show, we were all invited to hop up on stage after the last song for a photo – an end-of-show tradition for Rap J, and a fitting finish to a great night of Milwaukee music.
Rap J Setlist:
- “Boss Lingo”
- “Mister Inferno”
- “Rock Out (feat. Betty Mauritz)”
- “Freaky Good”
- “Salt”
- “Grateful”
- “Back in the Kitchen”
- “Ride”
- “Let’s Dance (feat. Tae The Don)”
- “Ric”
- “Speed Racer”
- “Unstoppable”
- “Don’t Sleep On Me”
- “The Way You Are (feat. Charlotte Webb)”
- “Roses”
- “Victory”
- “Medicine (feat. Riz)”
