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Video Vault: 5 Classic Wake Up Show Freestyles

Words by Daniel Isenberg (@StanIpcus)

While Stretch Armstrong and Bobbito Garcia were making radio history in New York City during the ‘90s, playing the newest underground records and introducing listeners to rap’s next superstars late night on WYNU, another duo out West in the Bay Area was also making their mark through the airwaves as hip-hop radio pioneers. Sway Calloway and King Tech, aka Sway & Tech (pictured above), were hosts of The Wake Up Show, which like their East Coast counterpart, featured new hip-hop music, exclusive artist interviews, and freestyle sessions. After a successful run on KMEL in the Bay Area, the show began simulcasting in Los Angeles and Chicago, and eventually, the duo made the move down coast to broadcast out of L.A. And of course Sway would go on to become a major player at MTV News, as well as the host of Shade 45’s current morning show Sway in the Morning.

In 1998, The Wake Up Show released a VHS tape featuring video recordings of their most memorable on-air freestyle sessions. It included clips of the dopest and most popular MCs from around the country, the most notable being The Notorious B.I.G.’s historic interview and freestyle in Los Angeles right before he was murdered in 1997, and Eminem’s career-breaking on-air appearance from later that year. So for our latest edition of Video Vault, we give you 5 Classic Wake Up Show Freestyles (as seen originally on their VHS release), including Biggie and Em’s, as well as three other performances that are particularly next level. Enjoy.

1. The Notorious B.I.G.

With Lil’ Cease to his right, Biggie got busy on the air with Sway and Tech just days before he was tragically gunned down in Los Angeles. After giving one of his last interviews—where B.I.G. refuted claims that he set 2Pac up the night he was shot in New York City at Quad Studios, and also shared his feelings surrounding Pac’s murder—Cease set off the session with some brief but dope bars over Sadat X’s “Stages and Lights” instrumental. B.I.G. followed with a pair of never-before-heard “Long Kiss Goodnight” verses from his yet-to-be-released sophomore double LP Life After Death, all while doing his own on-air edits. Watch how he rubs his eyes to the beat while he’s rapping, it’s bananas.

After a sincere plea, Biggie got the green light to curse from Tech, and flamed another exclusive verse off Life After Death from “You’re Nobody (Til Somebody Kills You),” over Mobb Deep’s “Hell On Earth” instrumental. It was a pretty risky choice of verses considering the climate of the time, but as we all know, B.I.G. bit his tongue for no one. Unfortunately, it would be the last time he would rhyme on-air live. RIP B.I.G.

2. Eminem

In 1997, an unknown Eminem flew out to Los Angeles from Detroit to participate in an event called the Rap Olympics. He came in 2nd place, and was granted the opportunity to join some of the other top spitters from the competition for an on-air cypher on The Wake Up Show. As Sway recalled for MTV, the mic went around for the second time, and Em went into his now famous verse over Biggie’s DJ Premier-produced “Kick In The Door” instrumental, rapping, “Met a retarded kid named Greg with a wooden leg/Snatched it off and beat him over the head with the peg/Go to bed with the keg, wake up with a 40…” So vicious.

As if that wasn’t enough, Em followed it with an even crazier verse, claiming that he’s “sitting next to ya’, eating a full course meal watching you starve to death” and  “pulling your Adam’s apple out through your mouth.” It wasn’t long before Dr. Dre got wind of Eminem’s talents and signed him to his budding label Aftermath Entertainment.

3. Pharoahe Monch

Queens duo Organized Konfusion paid a visit to The Wake Up Show during the promotion of their third LP The Equinox, and Pharoahe Monch stepped up to the mic and spit a ridiculous flow, rapping his ass off effortlessly with multi-syllable rhymes. Serious fans may recognize a piece of this verse from the Lyricist Lounge Vol. 1 radio clip of him spitting on-air with Black Thought, Common, and Absolute on Stretch Armstrong’s show, but that’s just the opening stanza. He brings additional unique heat for Sway & Tech.

Pharoahe remains one of the most underrated MCs of all-time, and this clip is proof that he’s worthy of more praise. As he raps, “You need to cop a shovel and dig it.”

4. Thirstin Howl III

We recently covered famed Lo Life rap artist Thirstin Howl III aka The Skillionaire during our interview with Dallas Penn about his favorite Polo pieces worn in rap videos. But Thirstin isn’t just a monster with the gear, he’s insane with the raps, too. And the barrage of wordplay and punchlines he displays in this freestyle clip over the Cocoa Brovaz (aka Smif-n-Wessun) “Won On Won” instrumental is second to none. There are too many quotables to list, but we love lines like, “I turn rap wannabee piranhas into A Fish Called Wanda,” and, “I freak the track like two Korean lesbians with pierced tongues.” Too ill.

5. Motion Man

Bay Area rapper Motion Man may not be a household hip-hop name, but nevertheless, dude killed this verse. Over East Flatbush Projects’ “Tried By 12” instrumental, which was a beat often given to rappers to rhyme over at The Wake Up Show during this time period, Motion Man freaked a wicked, unorthodox style, with made-up words, sound effects, pitch changes, and deadpan grills that you can’t help but laugh along with while watching. The cat to his left is cracking up during the whole verse. His delivery is mad funny, and dope as hell, too. You can see Tech laughing and rocking along to every word on the right side as well. It’s no wonder that him and Kool Keith formed a group together.

*The audio on this clip is particularly low, so crank to the max for ultimate enjoyment.

Clips via cprojux

Previously: Video Vault: 5 Pre-Reasonable Doubt Jay-Z Videos | Video Vault: 7 Classic Smack DVD Clips