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How Eastside L Boog's 'Teach U How 2 Jack' became a Milwaukee club classic

The video for Eastside L Boog's "Teach U How 2 Jack" doesn't look great by today's standards. In truth, it doesn't look great by its era's standards, either. It was filmed in the fall of 2009, on Sept. 11 to be precise -- you can tell because for much of the video the date is digitally stamped in the corner. Boog's friend volunteered to shoot the video because she'd just gotten a new camera, but she didn't make any big claims about knowing how to use it yet.

"It was horrible," Boog laughs, looking back on his breakout video. "It was shot on what looks like a camcorder. But mind you, we were teenagers. We didn't have no budget, nothing." There wasn't much planning involved, either. Boog and his collaborators simply started a text chain (they didn't use Facebook back then) telling their friends to show up in a park that day, and sure enough they showed up.

If it looks like that music video, now 11 years old, was filmed an eternity ago, that's because it really was from a different era of Milwaukee rap. Today's rap scene is a well-oiled machine, thanks in large part to a network of directors and videographers who know how to make it look great. Milwaukee rap has become, to a large extent, a visual medium, but in the late '00s hardly anybody had the resources to film professional videos, and YouTube wasn't the kingmaker it is today.

For Milwaukee rappers back then, there was only one path to success, and it ran directly through the clubs. "Back then, if you didn't have a club record, your record wasn't getting played," Boog recalls.

This is the story of how "Teach U How 2 Jack" became one of the biggest local club hits the city ever produced.

Eastside L Boog circa 2015

"This was energy music"

The late '00s were not a storied time for Milwaukee rap. Coo Coo Cal's 2001 hit "My Projects," the lone #1 rap hit to come out of the city, was long in the rear view, and Cal's exposure hadn't done much to put the city on the map. As "Teach U How 2 Jack" producer Young Tune recalls, "honestly the city was pretty dead."

"A couple people were making a little noise, but otherwise there wasn't a big music scene," Tune says. But what the city did have was parties. "People started going to underground parties, big bashes where artists would perform local songs," Tune says. "That's how the music scene began to develop into how it is now: It went from house parties to hall parties to club parties. Most of the people all knew each other, and everybody was a fan."

And so most of the Milwaukee rap from that era was made with crowds in mind. "The music had a lot of energy," Boog says. "We based it on lighting the clubs up. We also had this thing called traffic. We rode in traffic, and we just trailed each other, and the music would amp you up."

It was that energy that drew Boog to the nervy beat for "Teach U How 2 Jack," which had a hyper tempo that rivaled anything Soulja Boy was rapping over at the time. Young Tune explains that the average beat he was producing back then was around 200 or 210 BMP, a good deal faster than the 160-175 BMP tracks favored by the city today.

Tune was also a rapper -- he'd started producing his own beats out of necessity because he couldn't afford any he liked. Originally he'd hoped to keep this beat for himself, but eventually he sold it to Boog, who he figured was a better match for it anyway.

"This was energy music, and I specialized in that," Boog says. "I had the voice. Back then it was way more high pitched; it was me screaming over every track. Now I'm more calm, because everything slowed down. Back then I had all the energy in the world. I could get right in the studio and rap my lungs out. It was ridiculous and it was crazy, but it was fun at the same time."

Thanks to club spins and some radio support from the city's rap station, the song became a literal hot commodity in 2009 -- this was before music was widely streaming, when CDs still sold. "The song was on the first CD I ever made," Boog says. "We printed up a thousand copies and sold them for $10 a piece, sometimes $20. I sold out the first weekend I got the CDs out. So from that point on, the money was coming in. People would call up for the CDs, offering any kind of money for them. That was the whole summer of 2009. It was like a hustle."

Yes, there were memes

The song reverberated across the city, sparking its own style of music known as jack music, defined by its kinetic energy, woozy tempos and big boasts. The term "jacking" is Milwaukee slang for a number of things, but Boog mostly used it as a synonym for flexing or stunting -- at its core this was music about teens showing off the cool stuff they owned, or dreaming about the cool stuff they hoped to own.

And like most great rap trends, jack music was unabashedly youthful. "Most old heads hated it," veteran Milwaukee rap DJ Doc B recalled. "I liken it to this '80s house dance and song called 'Jack your Body,' where you jump up and down like a pogo stick and kinda run in place, but Milwaukee's version is way more aggressive and fast."

For a while, Boog said, jack beats were so common that Boog could literally spit the bars to "How 2 Jack" over most of the beats coming out of the city. "Young Tune really never got the props he deserved for pioneering that style," Boog says. "His template for the beats that he made for me started a whole movement."

"That song opened a lot of doors"

By the mid '10s, jack music started to take a back seat to Milwaukee's current preferred style of rap, known locally as slap music, and a new generation of rappers that's been able to find an audience on a scale local artists could have only dreamed about 10 or 20 years ago.

And yet jack music never completely went away. "Teach U How 2 Jack" still makes its way into DJ sets, and a little bit of jack music's DNA lives on in slap music, which for its grittier edge shares some of the same underdog sensibilities and playfulness of its predecessor.

"Jack music faded, but I feel like it's making a comeback," Tune says. "Rap is getting more geared toward club scenes and parties again. With Covid, people were tired of being trapped in the house so the club scene is starting to pick up again. I feel like the club scene is going to dominate it more."

Boog looks back on his breakout song with a mix of appreciation and regret. On one hand, he says, the video was a smash by the standards of its time. "We did 100,000 views, and nobody was doing anything like that," he says. "That was big back then. Nobody was hitting a million views."

But he also knows the track would have had so much more potential if it dropped today. "It wasn't what it could have been, if I had known what I know now about music," he says. "I would have licensed everything early, right away. I waited too long."

Still, he says, the song made local listeners pay closer attention to the Milwaukee rap scene, and it helped prime the stage for the rapid growth the scene has experienced in recent years.

"I wish it would have taken me further, but that song opened a lot of doors, both for me and the city," Boog says. "That song did its purpose."