About Jer-Bear

I am not a musician or singer. I am however an old soul at heart, which is why I think the Cubs have always appealed to me. Lord knows it hasn’t been their win/loss record. I’m a Polish Catholic Chicago guy who grew up in the “festering community of Lombard” with a mom, a dad, three brothers, two sisters and enough extended family and friends to fill up “Great America”. In the midst of a less than meteoric stand-up comedy career I fell in love with a gal who had an idea for putting a sock on the end of women’s tights. Thanks to Shelby and Bootights I can now add entrepreneur to my resume.

The full story of how The Cubby Chubby Song came to be is at the bottom of this page. Here’s a quick explanation for why it sounds the way it does: A catchy tune goes a long way so I chose a sing-a-long sound to give it that Barber Shop Quartet feel. Basically four guys in bow ties singing about being very excited about the Cubs. This style is both fitting and ironic considering that when the Cubs last won the World Series in 1908 the a cappella sound was considered “Pop Music” on the phonograph. I say phonograph because commercial radio was still years away! It turns out that the song “Take Me Out To The Ballgame” made it’s debut in 1908 as well.

While there is a double entendre element throughout The Cubby Chubby Song it’s playful words and melody make it a song that all Cub fans can relate to and enjoy. A song fun enough for kids to hum to and hokey enough for grandparents to join in. A song cool enough for dad’s to sing and wacky enough for mom’s to roll their eyes at. A song for a new generation to share and celebrate to.

Jerry Wolski – Cub Fan



About Chris Brown

The “Paul Schaffer” of team Cubby Chubby, Chris first brought Jerry’s words and melody to life back in 2003. Chris arranged and recorded the original version in studio by layering his voice to create a barber shop quartet sound. In anticipation of the Cubs winning the World Series in 2016, the Cubby Chubby song has been re-recorded with updated lyrics and is now sung by Chris and three talented buddies. Chris’s appearance in the Cubby Chubby cartoon as one of the members of the Barber Shop Quartet pays tribute to his talent, year’s of friendship and eventual hair loss.

About the Cubby Chubby Song

The words Cubby Chubby were first introduced into my life midway through the magical and devastating season of 2003 by my brother Tom, who shortly after another Cubs victory looked at me and said “Do you have your Cubby Chubby yet?” As a stand up comedian with an ear for funny and clever I knew that Cubby Chubby was a keeper. I wasn’t sure what I could do with it, I just knew it was too catchy to let die.

In June I found myself hitting the road for two weeks of shows in Colorado. As always, I timed my trek on I-80 to miss morning rush hour traffic and catch the Cubs game on the radio around the Mississippi River. The best thing about traveling west through the corn maze commonly known as Iowa back then was that even if you lost the old flagship WGN 720 there was always another affiliate on the dial carrying the Cubs game. Although scratchy and mixed among farm reports, the banter of Pat Hughes and Ron Santo during yet another Cubs victory was all I needed for the journey. With the precision of a submarine sonar technician I bounced from station to station to keep Sosa, Prior and Alou in the friendly confines of my speeding Chevy Prizm. As Nebraska moved closer and my signal became weaker, I happily strained to hear the final winning out. Aware that I was now in no man’s land, (sorry Council Bluffs) I triumphantly turned off the radio and my car went silent. To my total surprise, I then blurted out the opening line and melody to what would become The Cubby Chubby Song.

I had the first verse and parts of others done by the time I landed at the comedy condo of Loonee’s in Colorado Springs the next day. I tweaked the song on and off over the course of the run and finished it during the drive back. Entering the Land of Lincoln in full voice and after hours of odd looks from passing road warriors, I felt confident that I could sing the song through for anyone interested in listening to it. My brother Tom was my first audience and various drinking buddies my encore. With the Cub’s winning season taking shape and the playoffs a possibility I began to put “my band” together.

Now remember that it was 2003, the year that MySpace debuted and three years before anyone ever heard of something called YouTube. Reaching the masses was not as easy as it is today. I brought in Bob Schmidt a radio DJ buddy of mine from LaCrosse Wisconsin who was the only guy I knew who had a clue about websites on my budget. I found Chris Brown who was a member of a singing quartet in the Chicago suburbs and he agreed to arrange and sing my song by layering his voice in his home studio. I couldn’t afford all four guys. Once the song was completed we set it up so that it could be downloaded off of the Cubby Chubby website. I also had a local company produce 100 CD’s which I then mailed off to every radio station and DJ I thought would play it and hoped for the best.

The Cubby Chubby Song found initial success locally as well as nationally thanks in part to FoxSports Radio Host Ben Maller. Ben played The Cubby Chubby Song across the country on his overnight show and blew up our server with thousands of downloads. Unfortunately, the Cubs fell short in 2003. Like many fans, my heart was broken with four outs to go and the eventual realization that there was no “Sammy Klaus” who moved on shortly afterwards. While 2007 and 2008 were successful seasons, they just didn’t seem Cubby Chubby worthy. In fact nothing has…until now.

In appreciation for a very successful 2015 Cubs season and in anticipation of the incredible roster now in place, we’ve rebooted the Cubby Chubby website! Chris Brown and his buddies have re-recorded the song which now has an accompanying cartoon to go with it. The team at Kake Multimedia has done a fantastic job of orchestrating all facets of the relaunch and we look forward to future projects together. We’ll make adjustments to the site as needed and will happily take suggestions as we Cub fans move closer to our ultimate goal of celebrating a World Series.

On a personal note, I’d like to thank Shelby Mason for her love and support. She’s the only other person I’ve ever written a song for…and probably ever will.

Jerry Wolski – Song Writer