Stewart Winslow, reporting for duty!

In 1996 I was looking in the Comedy section at Sam Goody (heh, remember those places?) and happened across a cassette tape by a prank call artist known as Telephone Head. I’d never heard of Telephone Head before (Not to be confused with The Phone Heads prank call tapes!) so I immediately plopped down ten bucks for it. The label on it was D.I.L.L.I.G.A.F. Records, the same label that gave us The 976-Girls and The Ball Busters.

I’m not gonna say it’s the most hilarious collection of prank calls I ever heard, but they were mildly amusing. A few calls were kind of pointless, such as the one were he just calls up a guy and asks “How’s it going?” about a dozen times. But the best calls were definitely the Stewart Winslow calls. Stewart was a computer geek who got thrown in the garbage can at school a lot and was always in search of the best computer data processing center around. He also loved to tell everyone about his big penis. Take a listen to these Stewart Winslow clips:

Stewart Buys A Computer In this first clip, Stewart asks an old man questions about a computer he wants to buy.
Teen Crisis Hotline In this next one, Stewart calls up the crisis hotline to try and get help with his problems, such as all the other kids calling him keyboard teeth.

Stewart Buys A Car Finally, Stewart needs to buy a car that includes a computer data processing center in it.

A did a little searching around Google tonight, seeing if there might be a tribute page to Telephone Head, and I found a Telephone Head Myspace! It’s located at On their Myspace you can learn a little about the history behind the guy that made these prank calls and you can listen to the rest of the calls from his CD, which is good since I’m too lazy to create a torrent for them. And if you really love the calls, you can even buy the CD or tape from

Thanks for creating the Stewart Winslow character, Telephone Head guy! He’s brought me moderate chuckles for over a decade now. Hopefully you visitors will think he’s as mediocre as I do.

Brad Carter

I run this town.

6 thoughts on “Stewart Winslow, reporting for duty!

  • July 26, 2007 at 12:04 am

    Arby, don’t you have any tapes that are ALL funny? The Fightsters were entirely lame except for the name of Jesus, and they didn’t have anything to do with that.

  • August 3, 2007 at 11:42 pm

    this wasn’t funny.

    but i did like how much the teen crisis guy sounded like nawleed. too bad the call sounded scripted as hell.

  • March 9, 2020 at 11:42 am

    Yeah I was only 15 years old when I sign that record deal with the guys from the ball busters. I originally had over eight hours of material. basically they picked the calls they wanted to put on the album. which I thought pretty much were lame and not as funny as the rest of the material. back in 95 I was bootlegging tapes to everybody and my friends and it was spreading around. So a lot of the pranks I was able to upload them to MP3s. Trust me the album the artwork all that stuff I didn’t get much of a say so. They even wanted to name it a totally different name until telephone head got brought up and I told them that’s probably the best name you can give me all the other ones were lame. But like I said I was a 15 year old kid I somehow managed to get a record deal. I only sent two cassette tapes off the two different labels. So I spent my Summer of 95 making prank phone calls. a lot of trips of police officers knocking on my door also crazy ass phone bills my mother hated me for. And Stuart Winslow was just something I created on the fly I figured with that voice people won’t even take it seriously but I’ve had a lot of phone calls I did that they stayed on the line and listen to me. And that counselor that is 1 800 hit home. You’re always allowed to call from a payphone for free on it. and that’s how I did a lot of those calls to the counseling place for runaways and suicide stuff like that.
    Thank w.a.m.
    Aka The Real Munson

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