Mike Stack. CRICKET DESMARAIS/Keys Weekly

By Cricket Desmarais

Unless you’ve been living under this rock instead of on it for the last month or so, you’ve heard the up-tempo rap song, “I’m from Key West” by Mike Stack with fellow born-and-raised Conch D-Lew streaming out of the local radio airwaves and at the start of Conch baseball games. Stack’s 2 ½ -minute anthem for the people of the 33040 has everyone pumping their fists whether they live here or not, while plucking the heartstrings of those of us who do. 

“We’re coming from an island at the bottom of the map and we don’t take trash so if you talk crap, better hold that back. Hey! Hey! And the women stay pretty, and their drinks stay strapped. I’m gonna rep my city to the day I die — that’s a goddamn fact. Yeah, I’m from Key West. Yeah, I’m from Key West. Living where the sunshine stays, Southernmost City in the USA. …”

It’s a catchy, high-energy, yet tender tune, with a narrative that also reveals the underside of this sunshine island and the lengths many islanders go through to keep calling it home. D-Lew steps in for this part, rapping: 

“Right now this is good timing, so I’m gonna talk about Stock Island. We’ve come a long way since the ’90s. Back then it was wild’n but now we thrivin’, no lyin’. In my part of the Keys, sometimes ends don’t meet. Everybody ain’t rich and the rents ain’t cheap. Some people sell grams and they made me who I am. So rest in peace, Brooke and Marquis. When I die, put me right next to them. Yeah, I’m from Key West. Yeah, I’m from Key West. Living where the sunshine stays, Southernmost City in the USA. …”

Stack and D-Lew performed their island anthem at the Key West Weekly’s July 23 Bubba Awards, which named Stack Key West’s Best Local Celebrity. When he’s not searching for the perfect words for a new song’s chorus to get people singing along with all they’ve got, Stack pens custom songs for his friends’ birthdays and new babies, as well as jingles to help their businesses. He’s a guy who speaks freely of his love — for his island, his friends, and for the grandma who meant the world to him.  

“This place is so damn special to me,” says Stack. “Everything about this island — the people, the food, the businesses, the camaraderie, the atmosphere, the weather. I love it. Like, every day I wake up and I go outside and I feel it. I appreciate it so much.” 

If you went to Key West High School with Stack, who graduated in 2005, you might have known him as Big Daddy Mike, a name he wanted no part of. 

“I was like, this Big Daddy Mike name is just outta control. Yeah, I can’t have it. I need something else. I didn’t call myself that. I did it a couple times and I was like, no, I’m not doing that any more.”

A pal in college renamed him Mike Stack, given his deft ability to stack that night’s libations — “Natty Lites, tall and wide.” That was at Florida State, where he studied humanities, a backup plan to the communications program he had to forgo after letting his GPA get “disgustingly low” while at Tallahassee Community College.

“I took poetry classes. I took music classes and music history. So it was cool. It opened up a pathway,” he says. “I’m not upset I didn’t get the communication degree because maybe if I got that degree, I wouldn’t be where I am right now.”

Though Stack sang in choirs from the time he was a kid, it was college where he made his first song with nothing more than a borrowed MacBook Pro, complete with embedded microphone under the screen and built-in GarageBand software. He purchased a microphone in 2013, and made more songs over the next four years. 

“We made like six songs and we put ’em out. They did, well, nothing crazy. We just kept making more songs, making more songs. I’d make these spring break songs about Key West. And I did that for like five years in a row. We just couldn’t get it off the ground.”

But he’s OK with the time it took. 

“Rush, and it sounds rushed,” he says.  “I was just kind of taking it at my own pace, just doing what I do. I always had faith in myself. I knew if I kept putting out the music, something would eventually come. I knew we had to make one that was going to just really blow up the door and let all the other songs get love.”

When Stack says “we,” he isn’t referring to band members or managers. He has friends who guest on his songs, like D-Lew, but he is a solo artist who understands the collective nature behind a musician’s success. 

“Artists don’t become artists by themselves. We can make all the music, all the paintings, all the books. But if people can’t get behind it or aren’t gonna support it, then we’re nothing. The only reason I’m doing so well right now is because of the people who are listening. And that’s why I try to emphasize just how grateful and appreciative I am.”

As of late, Stack’s songs are streaming high across all the music platforms.

Who were your rap faves as a kid? Who inspires you now? My first rap CD was Nelly’s “Country Grammar.” My dad is from Scotland and had no idea about parental advisories, so he actually bought me the unedited version. It was a fun car ride home. He told me not to tell mom. Sorry, Mom! Nelly, Mannie Fresh, Lil Wayne, Biggie, Kanye’s “College Dropout,” I have a list. I think what inspires me the most now are the smaller artists who don’t stop chasing their dream and eventually get rewarded.