And It Don’t Stop: Milwaukee’s Hip-Hop Week Is What Happens When Hip-Hop Goes Back to Its Roots

Rapper Kevin Gates performs onstage during the PANDORA Discovery Den SXSW on March 18, 2016 in Austin, Texas.
Rapper Kevin Gates performs onstage during the PANDORA Discovery Den SXSW on March 18, 2016 in Austin, Texas.
Photo: Rachel Murray (Getty Images)

In 1994, Notorious B.I.G. would release his groundbreaking album, Ready to Die. The first single from the seminal hip-hop classic was “Juicy,” a Dickensian tale of a young black man’s ascension from having nothing to having everything, assuming, of course, that young black men can have Dickensian tales. The lyrics of B.I.G.’s first album have been combed over and dissected as if they were ancient etchings on Egyptian walls. I contend that the first line that B.I.G. rapped on his debut single from his first studio album might be its most important and the impetus for Milwaukee’s annual hip-hop week:


It was all a dream...

Who knew that Milwaukee is a city known for its music festivals and appreciation weeks? To hear 7th District Alderman Khalif Rainey tell it, they have a festival for just about every genre of music and weeks devoted to just about everything and that’s when it hit him: Why don’t they have a hip-hop week?

“For me, I was looking at all the weeks we have in Milwaukee like we have a fashion week and I was thinking to myself, ‘Why don’t we have a hip-hop week?’” Rainey told The Root. “I mentioned it to my wife and that’s when she brought some clarity to it.”

I believe it’s in the Bible’s book of Job(s) that states: Behind every black man’s dream is a black woman bold enough to help give it wings. Rainey, a self-proclaimed hip-hop head who isn’t shy to admit that his initial idea was more about music appreciation and very well could’ve died out with the alderman busting his best breakdance moves had his wife not stepped in to add structure.

I mean, sure, Rainey recognized the power of the music and the depth of the platform, but he’s quick to credit his high school sweetheart-turned-wife, Manadara, for helping to shape the event into what it’s become.

“We talked about how to connect it to some of the things that are important to the people that I serve and that’s financial literacy, civic engagement, and health,” Rainey said. “Ultimately what we concluded is that there is a lot of parity between these issues and hip-hop. In hip-hop they talk about money; they’re talking about getting their money right. In one way or another, they are talking about finances. So let’s bring people to the table who can put it in perspective and deliver a message that is palatable to this particular constituency.”


For the second year in a row, Milwaukee hosted the country’s only city government-funded hip-hop week that isn’t just a series of music concerts—of course, there is music; the climate-change-fighting super-shero from Houston, Megan Thee Stallion was supposed to headline, but she canceled at the last minute with an illness; but they also had Kevin Gates, Bun B, Devin the Dude, Do or Die, Benny the Butcher and more importantly, they got a gang of hip-hop legends talking about more than just hip-hop.

This year’s keynote speaker was Brad “Scarface” Jordan, who is taking his talents to public office as he’s running for city council in his hometown of Houston; Stic Man of Dead Prez hosted “Healthy Bars: A Hip-Hop Conversation On Health & Fitness” and DJ Envy, co-host of “The Breakfast Club” and quite the real estate investor, hosted “A Hip-Hop Seminar On Financial Literacy & Real Estate.”


Currently, Milwaukee is a gnat’s eyelash away from Memphis and New Orleans for being the worst area in the country for black homeownership. Just over 7 percent of the Milwaukee area’s African-American population owned a home in 2017, according to the latest data available. The median household income among African Americans in Milwaukee is $28,928 almost $20,000 less than whites in the same city. Milwaukee currently ranks 4th among major cities in the U.S.; in terms of children living in poverty at 43 percent. Alderman Rainey represents zip code 53206, which is 95 percent black and has the highest incarceration rate in the country.

The idea for Rainey was simple: use the music of the culture to get Milwaukee residents in the door and then use the power of the culture to get those who attend to stay and listen. It’s grassroots, old-school hip-hop street culture and barbershop politicking at its finest.


“How do we take these things that we are rapping about and turn it into political power?” Rainey said. “It’s one thing to talk about social justice reform but it’s another to say, ‘let’s form a political action committee, or let’s elect a candidate that reflects the things that we are interested in. Ultimately our approach is to put the medicine in the peanut butter.”

And who better to help inject the community with a sugar-coated healing elixir than hip-hop entrepreneur and creator of The Source magazine, Dave Mays. Mays was running the Hip-Hop Museum pop-experience, a visual trek through decades of hip-hop memorabilia. The collection has more than 500 pieces, including the iconic Death Row electric chair, mics signed by hip-hop legends Busy Bee and Brand Nubian’s Sadat X, and LL Cool J’s signed boxing gloves from the “Mama Said Knock You Out” video.


“There has never been a hip-hop museum before,” said Mays, who co-founded the museum with hip-hop collector Jeremy Beaver. “We are 45 plus years in now with hip-hop and its influence on world culture, obviously way beyond music in terms of its impact and there’s very little recognition in terms of its preservation.”

Earlier this year, Mays unveiled the pop-up collection in Washington, D.C. Rainey heard about the event through social media and contacted Mays. The rest was, as B.I.G. would say, “All good baby, baby.”


The two joined forces for the sake of Milwaukee in hopes that the music of their youth—which is still the music kids, teens, young adults, adults, and adult adults today—could be the bridge that merges apathy and action.

“There’s been a divide created between the younger generation and those are us that are a little older,” Mays said. “People between 18 and 55 represent 60 percent of the electorate next year and almost everyone in that age range has grown up in a world full immersed in hip-hop music and culture since they were young. If you are 55-years-old today, you were 15 when ‘Rapper’s Delight’ came out. So if we can bring the 18-year-old and the 55-year-old a little closer in terms of mutual respect and a mutual understanding in terms of the culture that underlies why they each like hip-hop in their own way, I think that can be very powerful.”


Alderman Rainey believes that the movement doesn’t just have to be a Milwaukee-based thing as he sees the potential for the event to take place all over the country. And while he wasn’t trying to brag, but he did note that his and Mays’ appearance on The Breakfast Club brought out a few politicians wondering how they could put on something similar in their city.

So if you’re in Milwaukee there is still a chance to take it all in as the event runs until Aug. 25. You can check out the line up here.


“And if you don’t know, now you know…”

Senior Editor @ The Root, boxes outside my weight class, when they go low, you go lower.


Yesha Callahan

I learned all I know about Milwaukee from Laverne & Shirley.