Weird Night at the Fair

September 2nd, 2010 | Posted in Freelancing

Me and “Weird” Al Yankovic

Some time back the lovely and extremely talented Sandra Boynton commissioned me into doing a caricature of “Weird” Al Yankovic for his 50th birthday. I was deleighted to do it because

1. Sandra is one of my favorite cartoonists and a wonderful person, and I was flattered to be asked.


2. “Weird” Al is to music what MAD Magazine is to comics, and I’m a longtime admirer of his.

Here’s the complete story if you want more details.

Shortly after Al received the artwork I received an email from him saying how much he loved it and how he was going to frame it for his home. He also said to let him know if I ever was in an area where he was having a show, and he’d get us some tickets and backstage passes.

Gabrielle, Anna and Tom show off their aftershow passes

Last night he played at the Minnesota State Fair, and I took him up on his offer. The Lovely Anna, daughter Gabrielle, son Thomas and I went to the show and met Al afterward.

The show was fantastic and he was a terrific guy, signing autographs for us and posing for some pictures in his trailer. I brought along some prints of a scan of the final artwork I did for him. The following will be framed and hung in the studio somewhere:

His show really was terrific, and I highly recommend seeing him live someday if you get the chance. It’s an evening of belly laughs and great parody with a lot of fantastic music snuck in there… Al is a highly respected musician even if he is better known for his humor. A great showman! Thanks, “Weird” Al!


  1. TDawn Maddox says:

    “Weird” Al is awesome, it’s great you were able to meet him. I was always amazed at how he could combine clever parody with a wide range of musical styles and vocal talent. Most music artists sound the same from song to song….”Weird” Al’s work is a new experience every song. .oh…and I’ll never forget watching The Weird Al show as a kid for the brief time it was aired.

  2. Ryan Roe says:

    Jason is going to be soooo jealous!

  3. Anthony says:

    That’s the most awesome thing ever. Weird Al is a musical and comedic genius. You’re so lucky.

  4. Weird Al Backstage says:

    Whoa! You got to meet Weird Al backstage? I am so jealous…

    I’ve been a fan of his for years. I worked in the radio business and have met just about everyone of my musical idols, but never Weird Al!

    Way to go!


  5. jailerjoe says:

    Weird Al, The MN State Fair, and family…PRICELESS! Great story, Tom. Ya sure that’s not Bucky under a wig, though?

  6. Nate says:

    That’s awesome, Tom! From what I gather (by watching interviews and everything) Weird Al seems like one of the nicest people out there in the music business. I was hoping to catch him last time he did a show here in St Pete, but wasn’t able to make it.

  7. Jason Cross says:

    His concerts rock me silly. I’ve been to 4. Have all his cds. So Crazy jealous over the backstage passes though. When he came july 12 to St. Charles, MO. I did a caricature of him and his band. Tried to get him to sign it but could only leave it with him. Never got to see his mug in person. What a night. Long live Al!!

  8. jimh says:

    Great shot of you and Weird Al, Tom. Also, nice painting – I had not seen that.


New profile pic courtesy of my self-caricature for the Scott Maiko penned article “Gotcha! Mug Shots of Common (but Despicable) Criminals” from MAD 550

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