A few months after moving back to Milwaukee in 2013, I found myself buying a cup of soup at the Public Market in the Third Ward. As I waited, I divulged to the woman behind the counter that I’m a hip-hop fan and have begun to write about local music.
The soup saleswoman told me she was a singer and gave me her name: Caley Conway. She also mentioned that her favorite rapper in town happened to be her roommate. Then she gave me his name: D’Amato.
Four years later, I’m interviewing D’Amato at the Milwaukee Art Museum. We’re sitting on black leather couches in a cozy nook overlooking Lake Michigan.
“When people talk about rappers in the city and I don’t get included I’m like, ‘Well, f*ck that. I’ll rap circles around people.’ And then when people call me a rapper I say, ‘Well, I’m not just a rapper.’ So I just can’t be pleased,” says D’Amato with a devilish grin.
The 28-year-old is not specifically referring to my story about meeting Conway, but generally emphasizing the fact that he is a multi-hyphenate powerhouse. Most notably, he raps, sings, dances, plays bass, guitar and saxophone. Most importantly, he is a showman.
D’Amato’s 2015 debut Counterfeit Paradise — distributed by local label Gloss Records — is one of the most interesting and entertaining Wisconsin records in recent years.
Since its release, D’Amato has assembled “the big band,” an 11-piece ensemble that has stormed onto the local scene.
By summer’s end, D’Amato and his band will have played at least five outdoor festivals, including the 88Nine Block Party on Saturday, June 24 and Summerfest on July 6.
Despite D’Amato’s big onstage personality, he is fairly guarded offstage. He finds interviews weird and I’m pretty sure he went “off the record” more than any other musician I’ve interviewed. This is what I’ve learned about the man they call D’Amato.
D’Amato’s family has roots in West Allis, a detail that he does not hide. In fact, he references the oft-maligned suburb on Counterfeit Paradise. He is the youngest of three children, with two older sisters.
“I feel like I was very much raised by women. As much as a feminine perspective as I could get, I got, and I’m grateful for it,” says the hulking D’Amato, who imbues his large frame with considerable grace.
While his father — a saxophone player in his youth — was his biggest musical influence, D'Amato's penchant for performance is inspired by his mother’s dramatic flair. As a child, D’Amato tagged along with his father at concerts and was compelled to create music at a young age.
D’Amato played saxophone in grade school. At a Turner Hall Ballroom show in April he revisited those days, playing sax and singing with his 8th grade teacher, Donna Woodall.
“She was a great teacher. I remember hearing her talk about being a musician and then I saw her play with her group, which was very inspiring. It fanned the flames that were already there,” D’Amato tells me.
In high school, D’Amato quit the sax because he didn't want to be in the marching band. But he joined a hip-hop/jazz/funk group called The Flow, which won a battle of the bands and played Summerfest in 2007. After graduating from Wauwatosa East the members went their separate ways. It would be almost a decade before D’Amato would assemble a band again.
'Right place, wrong time'
When D’Amato was 15 he shattered his arm, making it too painful to play saxophone and guitar. Until the age of 21, D’Amato was exclusively rapping. During that time he was heavily invested in late 1990s/early 2000s underground hip-hop, eschewing the popular rap music of the day.
At the age of 19, D’Amato moved to Minneapolis, a magnet for underground hip-hop heads. During his year-and-a-half residence in the Twin Cities, D’Amato kept himself busy writing and going to open mics, most notably at independent record label Rhymesayers store Fifth Element.
“Right place, wrong time. Just kind of out of my mind. Heavy in some sh*t I shouldn’t have been in. But what an amazing place. It was interesting from a music standpoint to see how a city works and then to come back and compare it to Milwaukee. It’s not drastically different, but coming back was a little sad. Things felt tense here in 2010,” D’Amato recalls.
'Out of the fog'
Shortly after moving back to Milwaukee, D’Amato met the guys at Higher Education Records. After two unsuccessful studio attempts, D’Amato joined forces with H.E.R. producer/DJ Moses and began work on Counterfeit Paradise.
“The process of writing it was great, but recording was the worst. Moses lived in Madison at the time, so I was driving there every Friday. It was just a hectic sh*t show and cost me a lot financially. From start to finish it took two and a half years. So by the time it came out I was just done with it.
"Also, the music I made doesn’t convey where I was at that point in my life. Three of my best friends had committed suicide. I lost some family. Breakups and what not.
"If your relationship with the inevitable, with death, goes from curiosity to obsession, from a respectable fear to a crippling fear, that can really mess your life up.
"When I’m in the midst of despair or depression, that’s not when I’m writing about it. It’s when I come out of the fog that I’m able to rationalize and comprehend it.”
The 'big band' forms
D’Amato began regularly gigging in 2012, but after a few years, he had grown tired of performing with backing tracks or a DJ. His friend Alex Heaton suggested they play together and add a few instruments. It snowballed from there.
“When you have those people onstage and you have their energy, you’re able to take it to a new place. It was a dream years ago. Now I have that, but these are all incredible busy people. Organizing 12 people is kind of a horrible experience. Playing with them is a climax. So now my dream is to have a band whose only job is to rehearse, put a show together and perform.”
D’Amato has one other dream — that Milwaukee audiences let go of their inhibitions and move.
“Do people here not like dancing? Or do they not know how to dance? I’ll get a very attentive audience and you can see that they’re focused, they’re into it, they’re enjoying themselves, but they’re incredibly rigid. I just want people to cut loose.”
Float like a butterfly
The first time I saw D’Amato was at the inaugural Arte Para Todos festival in 2015. It was also the soft opening of Company Brewing. The owner was carefully regulating capacity. Through the windows I watched D’Amato prowl the stage and drench his tank top in sweat.
He looked like a boxer.
“I have a deep fascination with boxing. As a kid I was enamored with Muhammad Ali. The only paper I ever got an ‘A’ on in the 5th grade was about Muhammad Ali. I have no formal training, but part of my pre-show routine is to go on stage in a sweat,” says D’Amato.
Gloss Records incorporated D’Amato’s boxing motif into the marketing campaign for 2016’s “Soul Low vs. D’Amato” show at Anodyne Coffee Roasters. That performance saw D’Amato ascend the railing at the back of the venue while the big band jammed. It would be a precursor to their breakout performance at Arte Para Todos 2016, in which D’Amato stripped down to his briefs for a guitar solo.
A profound experience
When D’Amato was a teenager, his father took him to a Derek Trucks concert at a theater in downtown Milwaukee. Opening the show an old bluesman from Chicago named Lonnie Brooks.
“Blues music was a big influence in the house, but I’d never heard the Lonnie Brooks band. He put on such an incredible show. We were in the balcony and at one point he came up into the balcony and was soloing. It was so theatrical and overwhelming, I was tearing up. It was the first time I’d ever seen someone putting on a show.”
There’s an element of that Brooks performance running through D’Amato’s big band shows. Derek Trucks’ performance from that night inspired another side of D’Amato, the R&B persona.
“My friend Rob just plays guitar and I sing. It’s very different from the live band, very tender, textured, soft, but it can get loud. I love the R&B project because I can stand in one spot and just focus on singing, close my eyes if I want and lose myself in the moment and deliver the music.”
The R&B project is somewhat of an offshoot of Rob’s group Cherry Ball, which D’Amato joined. The band is no more, but D’Amato says they cut a record and it’s really good. The new material he and Rob are collaborating on is being produced by Dave Wake of De La Buena — for whom D’Amato opened on his first big Milwaukee show.
The duo are also planning a European tour. After we talked at the Art Museum D’Amato went to meet Rob so they could take their passport photos.
'There's no plan B'
In between the big band shows and the R&B project, what keeps D’Amato going is the new material he’s writing. It’s not uncommon for him to sit down and work on music for 10 hours straight. He is a self-taught producer and currently uses Logic Pro, a MIDI controller, and always has his guitar and bass at the ready.
“Being able to sit down with no agenda and just absolutely free fall and see where it goes, that’s been the process. Things will take shape almost from a place beyond. You don’t see it coming and then it starts to form. Being able to get into that state of mind, it’s one of the things that I live for and I couldn’t do without.”
D’Amato’s hunger is undeniable. Writing and producing may be his fuel, which he can burn for hours in the studio, but onstage is where he lights up.
It’s only a matter of time before D’Amato is performing multiple-hour shows on a big stage.
“This is all that I have. There’s no plan B. All the eggs in one basket type deal. I know I need to play the online promotion game better. But just a note to the world, I will not let you down. I can’t.”