WebsterX: In the Van With Underground Rap's Golden Child

On August 11, 2016

Milwaukee's WebsterX is riding word-of-mouth performances and well-received, big outlet-premiered music videos to a wide acclaim that usually eludes rappers from Milwaukee. Will he be the one to put Cream City on the rap map? We had Michael Penn II follow the 23-year-old rapper as he wrapped up a U.S. tour in his hometown. Photos by Nikolai Hagen.    



It’s slightly after noon on a Saturday in May, and I’m eating a box of strawberries in a bluish-gray van full of tired young men. Some shirtless, one on a Macbook. Everyone looks dead tired.

A few days prior, on a ride from Chicago to Madison, the van almost fishtailed into suddenly-stopping traffic on a long hill. 27-year-old manager/DJ/graphic designer Nick Edmonds, a.k.a. Nick Magic, says this moment happened the one time his eyes and attention were completely on the road. A few days before that, the rear brake line caught a leak when they left Detroit. The aux cord is determined to amplify whatever bassline this van can muster, and it’s working; the highway to a near-summer Milwaukee sounds like Paul Wall and T.I. and the old Kanye. To get tired, right now, seems like a privilege the whole team earned.

23-year old Sam Ahmed, known in rap as WebsterX, has a broken-ish iPhone the day of his first Milwaukee headlining set in nearly a year -- he opened for Lupe Fiasco at Summerfest with the New Age Narcissism collective by his side -- and the penultimate stop of The Lost Ones Tour: an 11-city Midwest run featuring an assortment of the best musicians in the region like teen soul upstart Trapo to Florida-bred indie wunderkind Chester Watson.

The homecoming show was something of a potential coronation moment for WebsterX; after a couple years building a quietly ever-expanding fan base globally and in city, he’s on the cusp of being the first rapper to put Milwaukee on the rap map. The Lost Ones Tour was done with no major album or mixtape, instead, it was booked off the strength of singles and visuals. It all popped from the Noisey-premiered “doomsday:” a song with a clanging kalimba, rocking you like a violent lullaby during the end of the world. The video has Sam floating through the sky, faster than he can keep up, and is complete with running mobs of people and furious snowstorms. “Doomsday,” along with its successors “Lately,“ the Allan Kingdom-assisted “Kinfolk,” and “Everything” have grossed hundreds of thousands of listens, garnering cosigns from The Needle Drop, Pigeons & Planes, and even Jack White, who invited him to play his stage at SXSW last year.

We pull up to Bayshore mall for a collective piss break, and an Apple Store appointment doesn’t work out. But Sam doesn’t succumb to stereotypical millennial imagery, of not living a moment without his phone; the broken phone affords him a special peace of mind.


While WebsterX continues to climb towards amplifying his message to the world, Sam Ahmed grew up a shy guy. He’s a product of Ethiopian immigrants in a Muslim home on the Northside of Milwaukee; their neighborhood was predominantly Black, and a bit Jewish, with the family home being close to a synagogue. Sam went to school in nearby Wauwatosa, where he began to learn and internalize how whiteness functions. In “Renaissance,” he notes the frustration of being a “well-spoken token,” attributed to the duality of his daily life. He slightly hid his Muslim identity from kids on the Northside - some kids used to “rib,” or make fun of, his mother’s hijab - while dealing with white kids making fun of his hair and comparing him to Buckwheat from The Little Rascals, among other Black figures they saw on TV.

Sam became more extroverted over time, and came into his own as a creative later in his teens. He attended UW-Milwaukee for a few semesters, but dropped out because he was infatuated with the idea of music being the way he’d carve his mark in the world. He was living in a house on Bartlett Street on the Eastside, and threw several house parties where hundreds of locals would come rage to music. The carefree attitude of his youth is showcased in the scatterbrained vignettes of his 2013 Desperate Youth mixtape; the title track was written, and its video filmed, on the porch of that house on Bartlett. Produced by Milwaukee native Casey Soyk, a.k.a. CSYSYK, it was Sam’s first local breakout moment. But sometimes, youthfulness came at the price of that very desperation he speaks of, on a whim where carefree living can change based on careless action beyond control.

On the evening of February 2, 2013, Sam and his friends Joe and Sean decided to take an impromptu trip to Chicago to hang out with their friend Ryan at Hamilton’s, a bar they frequent on such visits. The crew stopped at the Famous Cigar shop on a snowy night in Wauwatosa, where Joe was robbed at gunpoint behind a building while Sam and Sean remained in the car. The gunman entered the car without knowing the other two were in the backseat. Sean let a noise out, causing the gunman to panic and give them five seconds to raise their hands and empty their things.

Sam and Sean obliged, then ran for their lives without turning back as the gunman sped off in the car with the doors ajar. The two ran through the neighborhood, eventually hopping a fence into a random backyard. As fate would have it, Joe ended up stumbling upon the same house; as Sam recalls, the family was just getting back from soccer practice. After returning to Bartlett that evening, the boys decided against souring the night, regrouped, and went on to Chicago anyway.

“Wauwatosa used to be the safest home / Until he pulled the chrome, pointed at the dome / Almost saw my mind, brain, visions blown / But I forgive the homie, none taken, holmes.”



At any moment, everything can end. But on the afternoon of May 28, Sam and the squad are doing a meet-and-greet at the Ian’s Pizza on North Ave. A few fans slide through to pay respect, ogle the Nick Magic-designed WebsterX tour t-shirt, and indulge in a slice before the main event. To date, WebsterX is the only rap artist I know with their own slice: grilled chicken, pesto, macaroni, and... mozzarella. “I almost forgot the last ingredient, but we good,” Sam says with a smirk. “It’s lit!”

A 23-year-old with their own pizza slice reads like a crown jewel, a real stepping stone for staking a claim and commitment to the Milwaukee pride that radiates off Sam. It’s also a testament to the inventiveness of Nick Magic: after coming on-board in winter 2014, Nick has overseen management and graphic design for the WebsterX brand as well as collaborative marketing efforts like the “WebsterX Slice,” which first appeared through a promo campaign for November 2015’s KidX EP: a three-track tribute to Radiohead, recorded over a year prior and released to tide fans over and add to the live repertoire.

Before linking up with Sam, Nick was on the same cookie-cutter monotony wave expected of most workers in the creative economy. But artist management is his dream job, and managing Sam is the first manifestation of a dream come true. Before rap, Nick taught himself how to DJ, learned graphic design, and became a handyman to fix gadgets around his house. Before receiving more critical attention, Sam went the classic route of reaching out through SoundCloud, Twitter, and Facebook like so many other MCs. The DIY energy is what drew them together, the pair says.

“We couldn’t be like ‘Yo, big rapper from Milwaukee, how did you do it?’” Nick says. “We just had examples, and we were like ‘Aight, how did they do it? We can do that.’ We had that mindset before the music industry.”

Milwaukee is becoming a cultural export in the regional conversation thanks to an indie scene that’s blossoming for the first time in a long time, from rappers like IshDARR to rock bands like Soul Low, Jaill and beyond. The biggest rappers from the city are Coo Coo Cal, who broke out with national rap smash “My Projects” back in 2001, and R&B-writer Rico Love, who finally broke through to mainstream in 2013 with “They Don’t Know:” a song my mom still runs faithfully on her iPhone. With older Milwaukee MCs not reaching far outside a regional radius, Sam had older MCs to learn from at a reasonable distance while plotting his own come-up.

“I just took a page from their book, but I also knew I could go a little farther,” Sam says. “Everybody’s tryna do their own thing and it’s really good, but it’s just the mindset of exceeding and getting out of the city. A lot of people are getting trapped here, very easily.”

I ask Sam if he feels like the OG in the music scene yet due to the critical attention he’s received after “doomsday” and “Lately” gave him traction the city, or state, hasn’t seen from its independent rap in quite a while. He’s quickly reluctant. “I feel like the OG requirement is 29 years old,” he said. I turn to his tourmate KennyHoopla to ask him what it’s like to be on his first tour as well. “I can’t… no clue,” Kenny says, with a dry chuckle. I ask him if he’s processed the last two weeks yet:

“No. I probably won’t either. No time to process, you gotta keep going forward.”



Later that night, some of the New Age Narcissism team pull up to the home of Carson “Mic” Kellogg, who’ll be the first set of the Miramar homecoming show. Several people are smoking and drinking, while Malik plays Minneapolis-based MC Finding Novyon in a game of NBA 2K. Out back, someone’s starting the grill up. Sam’s posted in the yard in a black jacket, feeling himself since he got a chance to shave all his tour excess off. He’s managed to keep this pensive energy about himself all day; an energy that’s fully-aware of the weight behind the show he’ll do three hours from now, yet complacent in his ability and the team around him. It’s an energy he’s carried on throughout the tour, which he calls “phenomenal.” Despite the name, the most lost he got was between hotels close to the venue, but the name isn’t only for him to abide by.

“If there’s anybody in the crowd that was ever lost, that’s exactly what this whole tour was about,” Sam says. “That’s why I wanted to call it The Lost Ones Tour: it’s based off the mask, my concept of depression that I’m just tryna push out to the kids. There’s gonna be a few kids who don’t really know what’s going on with their life when they come to a show; [We’ve been those kids] and I’ve met those kids before, too.”

The mask in question is named Lost Identity: a hidden talisman in the WebsterX journey that’s made appearances on Snapchat and marketing teasers, but most prominently in the visual for “Everything,” which plays out like an extended trailer for an afrofuturist summer blockbuster you haven’t seen yet. WebsterX literally crash-lands somewhere in the snowy forest, and the mask is somehow attached to his identity, though it isn’t fully-explained anywhere. I recall the way the squad was playing around with it earlier in Ian’s, as it sat on the table close to the t-shirts.

“If everybody else had that mask on, too… there’s not much judgment besides we all look the same,” Sam says. “When you take the mask off, that means you’re comfortable in this world and you can exceed and keep doing what you want to do. Everything behind that concept is what I set out for myself; I’m tryna bring that [to life.]”

Furthermore, what does the X in WebsterX mean? Is it a nod to the aforementioned afro-futurist undertones in lines like “Vivid visions of a young Black god on a mission” or a mere placeholder to acknowledge the history of our nation? 

“It’s the loss of [my] identity entering into music and the industry,” Sam says. “I am what you get, there’s no extra gimmick - cuz we know a lot of those gimmicks exist - it is what it is.”

Sam is very big on visions; so much so, he had this fantasy where he felt like the only one on Earth, peering into his own future like a golden child destined to change the world. While the tour was a major success, Sam’s not oblivious to the mounting pressures of maturing into a Black anything, let alone a successful artist. Wisconsin’s faced two police-involved shootings of unarmed Black men in the past two years: Milwaukee’s Dontre Hamilton, who was shot in Red Arrow Park in April 2014, and Madison’s Tony Robinson, who was shot in his home in March 2015. Neither officers were indicted, and Sam assures me that NAN feels that pressure and acknowledges such responsibility to be leaders in the communities they represent.

“What I’m tryna do is make people forget, because we have to forget sometimes to move forward,” Sam says. “The only thing is, I need the team; I can’t do it by myself. I can help organize thoughts and try to find [the balance], but I think it’s gonna get heavier for me the bigger I get if there’s crazier shit happening in the world. If there’s more wrongful shootings in Milwaukee, or Wisconsin, I’ma step up. I can’t sleep at night knowing shit is in shambles. If I can do something - and I know I can cuz I got big influence - I’ma do it, all day, every day.”



The Miramar Theatre promises a wild situation: it’s a 400-seat venue with the vibe of a haunted movie theatre, thanks to the awkwardly-placed seating and standing sections on either side and the oversized projection screen. It was a punk and metal venue for the scene kids of Milwaukee, now converted into a dancery for primarily EDM heads, but a few good larger-scale indie rap shows like this one. The kids are dressed to kill, with their influences heavily on their sleeves, but the energy is immaculate and the camaraderie is a visual alternative to the fountain of youth.

Somewhere in the madness, about thirty minutes before Sam and NAN take the stage, the greenroom is cloudy with weed smoke and libations abound. But there’s some other shit going on here, too: Sam’s trapped in the bathroom. No, he’s literally locked inside it like something out of a nightmare before the biggest gig of your life. It took three different people to try to unlock the door from the outside until the homie/frequent collaborator Pat kicked it down and freed him to a massive applause. I wonder if he saw that deeply into the future, but just focused on giving him dap and laughing it off.

What I see in the forty-minute WebsterX show, is an experience that works to channel every energy it can, only to reverberate it all back into the room. There’s a set piece where drummer Chris G and pianist/producer Q the Sun leave their instruments to hit a dance routine center-stage while their KidX medley spirals out of control into a house-electro noise section. It sounds like the information superhighway if you could whip to it. The “NA-NA-NA-NA-NAN HEY!” chant is heard throughout. Singer/songwriter Siren throws water on the crowd for the second first time this weekend; she tried the night before in Madison, but it was nowhere near as successful. The squad ends on “Desperate Youth” as they’ve done many-a-time before: mobbing the stage with almost everyone from backstage, bowing down like warriors on one knee waiting for the ebb-and-flow of the beat to reach its climax before moshing as an uncontrollable unit. Some kids end up moshing in the crowd, and Sam is clearly caught in the moment despite being dead-set on giving this crowd the same show he’s given for the past two weeks.

It was easy to observe how proud everyone was backstage, but you could see Sam grappling with the visions of his own future when he goes momentarily silent between set transitions. He’s clearly cherishing the night, the sweat, the strobe lights and fake palm trees that are mere precursors for whatever he’s planning to release in the fall.

Sam still feels like that lonely golden child, but cites this time as “the most difficult stage of his life.” It’s feasible, considering he’s never fully confronted his depression and anxiety head-on. He tried to catalogue these struggles through an album, all of which he scrapped since he felt the need to capitalize on his rising success off how far Desperate Youth got his team. Perhaps he worried more of creating a huge platform for himself and everyone around him, which may have cost him the self-care needed to process that pressure. Spending all one’s focus on the future is an easy formula for missing the moment in right now; from the eyes of Sam Ahmed, there’s a hell of a moment happening right now. If that night at the Miramar is indicative of that vision, there’ll be plenty more to come.

For now, it’s best to wish godspeed to the golden child.

Profile Picture of Michael Penn II
Michael Penn II

Michael Penn II (aka CRASHprez) is a rapper and a former VMP staff writer. He's known for his Twitter fingers.

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