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Looney tunes

Musical comedian Will King mines current events for playful parodies

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Will King and his trusty guitar will be staples at this year’s Great Outdoors Comedy Festival.

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Will King and his trusty guitar will be staples at this year’s Great Outdoors Comedy Festival.

The 37-year-old musical comedian is set to warm up the crowd with satirical songs and well-known covers prior to each headlining slot during the three-day festival, which kicks off Friday at Assiniboine Park.

Supplied
                                Will King will warm up the crowd with musical comedy prior to each headlining slot this weekend.

Supplied

Will King will warm up the crowd with musical comedy prior to each headlining slot this weekend.

Born in small-town Kentucky, King moved to Nashville in 2009 to pursue a career in songwriting. He worked at Tootsie’s World Famous Orchid Lounge on the Honky Tonk Highway and has written songs with the likes of Lainey Wilson, Brothers Osborne, AJ McLean from the Backstreet Boys and JC Chasez from ’N Sync.

His songwriting gigs dried up during the pandemic and he turned to social media to share the comedic songs he was making in his spare time. He gained a large following on Instagram (@willkingmusic) and has since turned comedy into a full-time job.

Free Press: When did musical parodies become an interest? Was standup comedy something you ever envisioned doing?

Will King: Parodies and comedy in general have always been a big part of my life. One of the first CDs I ever owned was the “Weird” Al Yankovic Running With Scissors album; I got it when I was 10.

Years before posting my first parody and comedy song online I always tried to make my wife or friends laugh with some dumb little parody or joke I came up with.

And in songwriting sessions, I would always try to throw in a little humour or a witty line in a song. I’ve kind of always been searching and working for the laugh.

FP: Who is your favourite musician? Who is your favourite comedian?

WK: My all-time fave musician would have to hands down be Jason Mraz — for his wordplay and how he slips a little humour in his songs every now and then. I also remember thinking, “Wait, this dude sings and raps and does them both well?”

Eddie Griffin and Lewis Black definitely were my first two favourite comedians growing up. Katt Williams stands out now as a current favourite and Rodney Carrington was the first to show me that you could be country, comedic and play the acoustic guitar

FP: Walk me through your creative process: does the commentary come first or do the songs serve as inspiration?

WK: Usually the commentary comes first, I would say about 99 per cent of the time. I typically need to know why and what I’m writing about first and then I’ll pick the song after that I think best fits with the idea.

A lot of my views come from me singing about the news and trending TV shows and celebrity gossip, so once I see what everyone is talking about, I find my point of view on it and then pick the song because I know I gotta be quick.

FP: How long does it take you to work out a song?

WK: It honestly changes from song to song.

I was loading the dishwasher when I wrote the entire first verse and chorus to my Stacy’s Mom Fountains of Wayne parody — probably took me 10 to 15 minutes to write and another 10 minutes to record it.

I posted it, not thinking it would get 125 million views. Then on the flip side, I’ll have songs that take me up to three to four hours to really chase down.

FP: Is there a genre, an era or a kind of song that works particularly well as a satirical number?

WK: Definitely! I have found that the song either has to be one of the biggest songs of the moment — a Choosin’ Texas by Ella Langley parody would do incredible right now but in a couple of months it probably wouldn’t catch on — or a timeless classic that no one will ever forget and will know instantly, like Don’t Stop Believin’ or Hit Me …Baby One More Time.

FP: How does it feel to have made a career out of music, even if it’s not how you pictured it?

WK: Even though I did not have a musical comedy career on my bingo card, it honestly feels amazing and I wouldn’t trade any of this for what I thought I wanted when I first moved to Nashville in 2009. Seeing people comment about how my silly songs and jokes make their day better is worth more to me than any Grammy.

This interview was conducted over email and has been edited for length and clarity.

eva.wasney@winnipegfreepress.com

Eva Wasney

Eva Wasney
Reporter

Eva Wasney has been a reporter with the Free Press Arts & Life department since 2019. Read more about Eva.

Every piece of reporting Eva produces is reviewed by an editing team before it is posted online or published in print — part of the Free Press‘s tradition, since 1872, of producing reliable independent journalism. Read more about Free Press’s history and mandate, and learn how our newsroom operates.

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Updated on Thursday, July 16, 2026 5:27 PM CDT: Moves second story to new file.

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