“Hip Hop Confessionals” Live Podcast and Trivia Game on a Stand-Comedy Stage with Mad Skillz

Norfolk, VA’s Shaquan Lewis has, since the mid-90s, been better known as Mad Skillz, and best regarded for a tough, smart brand of freestyle rap that made him the envy of fellow flowacists for his mad prodigious rhyming talents. And even though his Atlantic Records debut (1995’s From Where???) sadly went nowhere and a recording contract with Timbaland’s Blackhand label failed to gel, Mad Skills made. 2002’s I Ain’t Mad No More on the Rawkus label with features from The Neptunes and Missy Elliot, and moved into a career on the web of hosting his self-created series “Hip Hop Confessions. Mad Skillz’s “Confessional” web program – funny and poignant – offers a look at the literal insides of hip hop (or whatever its participants dare reveal) within the intimate confines of studio.

Now, Mad SKillz is taking his show on the road, to the stand-up comedy clubs of America, starting with Punch Line Philadelphia on March 27, with a live podcast and trivia game-based showcase “Questions and Confessions.” This “ultimate hip hop experience” – with live contributions from the host’s long list of in-the-biz friends and interaction from the night’s audience – promises to be as funny, frank and revelatory as anything Mad Skillz has been up to across the last three decades, and as intimate as a barbershop for real life conversation.

Philadelphia Weekly’s A.D. Amorosi hooked up with Mad Skillz for a hip hop confession right before the start of his live showcase.

A.D. Amorosi: Like a Joe Budden, you moved from a successful career as a rapper into web content and podcasting.  Can you please tell me a little bit about the whys and hows of moving from live rapping into podcasting? And what you believe is a tougher job: rapping or podcasting/web content hosting?

Mad Skillz: Yea, I started Hip Hop Confessions in 2009 before podcasting was even a thing. I knew that the conversations that I would have with my friends in private, and then in the barber shops were very important conversations. We would talk about things that we normally wouldn’t talk about in public because we were amongst friends. And I realized that a lot of people had Hip-Hop Confessions, but not necessarily would want to admit those things in public and then I came across the notion that I had friends that WOULD admit these things in public, and that’s when the lightbulb went off.  Podcasting is really easy to me because I can talk about hip-hop all day. Rapping takes a lil’ more out of you.

A.D. Amorosi: I know your work as a rapper/writer quite well. How would you qualify and quantify your level of artistry and years in the rap game?

Mad Skillz: Hip Hop is now 50 years old, so some of us have been around since the beginning and the thing about being able to adapt is something that I don’t think a lot of people pay attention to the base of everything for me is music… I love music. everything that I’ve done falls under that umbrella, I like rapping, I like deejaying, I like writing for others, I like teaching, but I love music. Music is and always will be the common denominator for me in everything I do.

A.D. Amorosi: You have taught at the University of Richmond; a class entitled The Voice of Hip Hop in America.  How do you teach hip hop?

Mad Skillz: When we teach it, we teach it as a social and political movement. Hip Hop is the most popular form of music and has been for the last 30 years so some of these kids have grown up on it but their knowledge of it might’ve started when they started listening, so if you started listening to hip-hop when Eminem became popular, there is a whole window of music and culture that you actually missed out on. Our course starts at the beginning of hip hop and goes up until when Obama was elected. It is a broad spectrum that we cover, but we cover it all.

A.D. Amorosi: What can you tell me about the reasons for developing the web series “Hip Hop Confessions”, in the first place, and how you got artists so usually guarded (say  Q-Tip and DJ Jazzy Jeff) to open up, go deep and talk?

Mad Skillz: I was able to get those type of confessions because, initially, when I sat down, the people I sat down with were my friends. We had had those conversations off the record already. Among us. The problem was never getting people to tell me their confessions. The problem was getting them to tell me their confessions on camera. After a while, I stopped doing a Hip-Hop Confessions because it was hard to get people to be honest on camera. I stopped for about a year and then the podcast world  happened and everyone kept asking me to bring it back. That’s when I knew I had something.

A.D. Amorosi: Without offering a name – unless you can – what was the most surprising confession you ever received?

Mad Skillz: I have had one guy reveal to me that he did not know that Shock G and Humpty Hump was the same person. That one was wild. I still shake my head at that to this day. I also had a girl tell me that up until Straight Outta Compton was released – The Movie- she thought NWA was one person. I don’t even know how that is possible! (Laughs)

A.D. Amorosi: Revealing secrets online is one thing. Revealing secrets and discussing one’s personal and professional triumphs and tribulations in person – on stage – is quite another. Tell me something about bringing Questions and Confessions to the stage?

Mad Skillz: What we’re doing with Questions and Confessions is creating a space where people can be honest, and be OK with being honest. That and itself hasn’t been done and Hip Hop and the crazy part about it is if you’re truly honest about something, you would probably be surprised at how many people may feel the same way and then we open it up and have a discussion about that. That’s where the magic is when it comes to Hip Hop Confessions! The Questions is the Hip Hop Trivia portion of the night. That was created by my co-host Sean Kantrowitz. He’s a beast when it comes to hip hop trivia, and none of this would be possible without him. I mean how many opportunities do people have to sit down with Mad Skillz, Freeway and Peedi and actually beat them in hip hop trivia? That’s gonna be fun! I can’t wait.

A.D. Amorosi: So, what is so funny about the hip hop confessionals that you hope to get out of your confessing visitors to warrant their entrée onto a comedy club stage such as Punch Line?

Mad Skillz:  I want them to realize that this is a safe space, and everyone doesn’t like everything, or like the same things. And everyone doesn’t know everything about hip hop – so let’s discuss it. My Top 5 MCs may not be the same as your Top 5 MCs. This is the space where we can discuss that in a room full of people that love hip hop. You just can’t get a haircut in there!

    • A.D. Amarosi's Headshot

      A.D. Amorosi is an award-winning journalist who, along with working for the Philadelphia Weekly, writes regularly for Variety, Jazz Times, Flood and Wax Poetics, and hosts and co-produces his own SoundCloud-charting radio show, Theater in the Round for Pacifica National Public Radio station WPPM 106.5 FM and WPPM.org.

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