When life gets too overwhelming, sometimes all there is to do is hit snooze. For Alexander Fruchter, a power nap during one of his rock-bottom moments turned into the birth of Legend Conversation—a live interview and dinner series featuring some of the most notable and heavyweight names in the Hip-Hop Hall of Fame.
“I woke up and felt almost like all the negativity somehow washed away,” Fruchter said. He had woken up to the news that Raekwon and GZA from Wu-Tang Clan were hitting up Chicago on their 2021 tour.
Fruchter felt his inner music journalist stirring. After running the hit hip-hop and culture blog rubyhornet (which he founded in 2008) and Chicago-based record label Closed Sessions (founded in 2009), he was itching for a way to reconnect with his journalism.
“The concept was an intimate night with these artists. I think there’s a lot of people that want that connection that a concert doesn’t really offer,” Fruchter said.
Legend Conversation originally kicked off with its first two chats at SoHo House Chicago in 2018. After a COVID-19 hiatus, Frutcher wanted the series to come back with a bang. He reached out to Raekwon to be a special guest during the 2021 tour, and the Chef joined for an interview between Chicago tour dates.
The series made its South Side debut this year at its eleventh event, which featured Canadian DJ and record producer A-Trak, the Conversation made waves at the newly opened Ramova Theater in Bridgeport on April 11.
“I started this series way back to be around new people, spark these collaborations, tell the stories and then to be able to do it at Ramova was awesome,” Fruchter said. “Bridgeport wasn’t even a place that we hung out when I was a kid.”
Bringing A-Trak was a treat for many South Siders who remember him not only for winning the DMC World DJ Championship at the age of fifteen (making him the youngest person to do so) but also for being Kanye’s tour DJ. A-Trak’s superior turntable and scratching skills have cemented him as a respected figure in hip-hop. He’s gone on to found and run the record label Fool’s Gold.
For Legend Conversation, he ended the night in the booth delivering a high energy and enthralling set. The show was a full-scale production with special guests like Chicago-based rappers femdot. and Jay Wood, and DJs including DJ Ca$h Era and Eva Maria.
The repertoire of collaborators is extensive, one of them being Jugrnaut, which produces a collector’s T-shirt designed with the featured artist in mind. The eleventh Conversation tee, sold exclusively at the event, sported a Chicago-style hotdog duck, a nod to the DJ duo Duck Sauce, made up of A-Trak and American DJ Armand van Helden.
Credit: Alejandro Hernandez
The interviews are tag-teamed by Fruchter and his partner in the revamped Legend Conversation, Hyde Park local Dave Jeff, a streetwear trailblazer and influencer. Fruchter begins prepping weeks ahead, diving into blogs and past interviews so he can serve up a cocktail of questions that can satisfy devoted fans and newbies alike.
Among the crowd at the Ramova were Ric Wilson, Sir Michael Rocks, Don C, and Chicago’s own blogfather, Andrew Barber, creator of Fake Shore Drive.
“I got a VIP card now. I get like a punch card cause I’ve been to so many,” Barber joked, noting that he’s only missed one of the conversations.
“It’s a good crowd, good networking, I meet younger new people that might be up and coming on the scene, new DJs that I’ve never heard,” Barber said, gesturing towards returning DJ Eva Maria.
That’s one of the unique aspects of Legend Conversation: it’s intentionally multigenerational. This allows not only established figures in the scene to be recognized but also provides a platform for discovering and showcasing new artists.
“These culture makers, these people before us laid down a foundation that we need, that we enjoy today,” said event producer, award-winning Chicago journalist (and, full disclosure, my friend) Jesus J. Montero.
Montero joined the team after Fruchter revamped the series following the pandemic in 2021. Since its relaunch, names such as The Alchemist, DJ Premier, Jazzy Jeff and even returning artists like Bun B have become part of the line-up.
“[The] main focus at the end of the day is honoring those before us,” Montero said. “As long as we do that, then we did our job and anything outside of that is just a pure blessing.”
The series has amassed several sponsors and partners, such as RYTHM cannabis company, which handed out free mini-joints for guests to enjoy at the event. Ramova allowed for open consumption in designated areas, potentially setting a catalyst for smoking sections to make a comeback.
“It’s a communal experience, puff, puff, pass; it is about sharing. And I just think it’s awesome that the government and laws have caught up to people and to be able to have these events,” Fruchter said.
Looking ahead, Fruchter wants to add variety and bring more women into the mix. “We do try to really focus on that inclusivity and showcasing as many different people as we can,” he emphasized, noting the variety in age, gender, and ethnicities at his events.
He hinted at an upcoming video and podcast series derived from Legend Conversation. For Fruchter, whose passion for journalism intertwines with his love of music, this series has been a dream come true.
“I just wanted to interview and talk to my heroes,” he said.
Jocelyn Martinez-Rosales is a Mexican American journalist from Belmont Cragin and the Weekly’s music editor.
