iiinova — where your digital self keeps evolving

Jason Benefield @jasonbenefield.com · 21/09/2026

My next Song Swap at Black Dog Vinyl Cafe is coming up this Friday, 9/25, and I’ll be welcoming the incredibly talented Jackie Carol as my very special guest. Come hang out and hear some songs and stories. Q4 Song Swaps are booked and dropping soon! #music #singersongwriter

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Jason Benefield @jasonbenefield.com · 17/09/2026

Musing on “Broken Things.” Experience the whole thing, including lyrics and whatever my left hand is doing, at Vintage Illinois Wine Festival this Sunday at noon. #music #musician #songwriter #acousticguitar #fingerstyle

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Jason Benefield @jasonbenefield.com · 14/09/2026

Last year I played guitar for my buddy Aaron Kelly at the Vintage Illinois Wine Festival in Utica. This year, I’ll be back for a solo set on Sunday, 9/20, at noon. Grab your tickets now. #music #livemusic #songwriter

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Jason Benefield @jasonbenefield.com · 09/09/2026

“When you cut this city it bleeds orange and blue.” It’s the most wonderful time of the year. Bear down, Chicago Bears.

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Jason Benefield @jasonbenefield.com · 08/09/2026

Celebrating 6 years of Black Dog Vinyl Cafe (and 9 years of E&R) this Saturday night!

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Jason Benefield @jasonbenefield.com · 07/09/2026

Coming up: • E&R at Black Dog Vinyl Cafe in Plainfield for BDVC’s anniversary weekend on 9/12. • Solo at Vintage Illinois Wine Festival in Utica on 9/20 (tickets on my website and theirs). • Song Swap at BDVC with Jackie Carol on 9/25. #music #songwriter #livemusic

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Jason Benefield @jasonbenefield.com · 03/09/2026

I’ll be at the Aurora Farmers Market bright and early this Saturday, 9/5. Last market set I’ve got in 2026, so swing by and shop local. #music #livemusic #supportlocalmusic #songwriter

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Jason Benefield @jasonbenefield.com · 26/08/2026

This Saturday I’ll be headed up the Fox for an afternoon set at Riverlands Brewing in St. Charles. 2:00-5:00pm. #music #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 26/08/2026

Dolly Parton was a profound influence on me as a musician, and, more importantly, an inspiration as a human. Lots of people tell you how to live. She just showed you. I already miss her 🦋

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Jason Benefield @jasonbenefield.com · 18/08/2026

I’m very excited to share the Black Dog Vinyl Cafe stage and swap songs with the remarkably talented Heather Mall this Friday night. You don’t want to miss this. #music #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 14/08/2026

It’s been a dream of mine to have a song played on WXRT. This Sunday night, I’m elated to announce that the legendary James VanOsdol will be spinning “When I Get Old” on Local Anesthetic. Make sure you tune in this week and every week, and thanks to JVO and XRT for showcasing Chicagoland artists!

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Jason Benefield @jasonbenefield.com · 13/08/2026

Looking forward to a lovely afternoon this Sunday at Blind Corner / Go Brewing in Naperville. Swing by and I’ll sing you some songs. #music #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 12/08/2026

E&R will be at The Venue in Aurora, IL on Saturday night supporting our friend Mirabelle Skipworth. Grab your tickets.

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Jason Benefield @jasonbenefield.com · 31/07/2026

I’ll be walking the streets of Lockport, IL this Sunday afternoon with my friends, supergroup The Petty Bettys, to raise some cash and awareness for Guardian Angel Community Services. Come see us!

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Jason Benefield @jasonbenefield.com · 29/07/2026

Haven’t shared a stage with my buddy Nick Wiesner in too damn long, but we’ll be swapping songs this Friday, 7/31, at Black Dog Vinyl Cafe. Come hang out with us. #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 27/07/2026

One of the most fun White Sox games I’ve ever been to. Murakami hits 2 dingers and plates 6 ribeyes on his friggin’ bobblehead day? Magical.

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Jason Benefield @jasonbenefield.com · 24/07/2026

I’ll be playing some songs at the Aurora Farmers Market bright and early tomorrow morning. 8-noon. Shop local. Listen local.

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Jason Benefield @jasonbenefield.com · 24/07/2026

I strung it myself, by the way.

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Jason Benefield @jasonbenefield.com · 23/07/2026

I’ve got one last gig at Brother Chimp Brewing’s North Aurora location tomorrow, 7/24, at 6pm. It’ll be an original-heavy set. Who’s coming? #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 20/07/2026

This weekend: 7/24 at Brother Chimp Brewing in North Aurora for the last time. 7/25 bright and early at the Aurora Farmers Market. #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 17/07/2026

Next Friday, 7/24, I’ll be playing one last gig at Brother Chimp Brewing’s North Aurora location before they shut the doors for good. It’ll be an original-heavy set. Swing by. Hang out. Chimp puns intended. #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 17/07/2026

Just added! I’ll be playing a free afternoon set in the Hey Nonny bistro on 7/18 before Covington Groove lights up the main stage. Reserve a table in the bistro and grab tickets for the main stage show on the Hey Nonny website. #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 07/07/2026

It’s been too damn long since we’ve been done an E&R gig at Skeleton Key, but we’re rectifying that this Saturday night. Come see us! #music #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 01/07/2026

Hey wake up. New batch of Song Swaps at Black Dog Vinyl Cafe just dropped. Special guests: 7/31 Nick Wiesner 8/21 Heather Mall 9/25 Jackie Carol #livemusic #songwriter #supportlocalmusic

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Jason Benefield @jasonbenefield.com · 30/06/2026

Streaming pays a fraction of a penny, but merch sales keep gas in the tank. Head over to jasonbenefield.com/store and grab a shirt or something, would ya?

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Jason Benefield @jasonbenefield.com · 25/06/2026

Hey Chicagoland. Come out to Milkstop in La Grange, IL on Saturday, 6/27 and I’ll sing some songs for you.

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Jason Benefield @jasonbenefield.com · 24/06/2026

The White Sox won and my birthday wish was granted. By the way, come see me Saturday night (6/27) at Milkstop in La Grange from 8-10. We can chat about the Sox or Supergirl. Mostly it’ll just be me singing.

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Jason Benefield @jasonbenefield.com · 23/06/2026

46 All I want for my birthday is for you to go stream some of my songs on your streaming service of choice. Maybe share them with your friends, too. Also, I’m going to the White Sox game tonight so if they could win I’d appreciate it 🥺🙏🏻

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Jason Benefield @jasonbenefield.com · 16/06/2026

I’m heading to Preservation in Geneva, IL tomorrow, 6/17, for some midweek catharsis. Let’s spend some quality time together. #livemusic #songwriter #localmusic

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Jason Benefield @jasonbenefield.com · 12/06/2026

“Rich Man” has been out for a week now, and I’m so grateful to those of you who’ve taken the time to listen to it. I wrote this song about…well…*gestures broadly.” If you haven’t given it a spin yet, I’d really appreciate it if you did. It’s streaming everywhere.

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Jason Benefield @jasonbenefield.com · 10/06/2026

One week until I’m back at Preservation in Geneva, IL for some midweek catharsis. 6:30pm kickoff on 6/17. Come hang out. #music #songwriter #livemusic

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Jason Benefield @jasonbenefield.com · 09/06/2026

Saturday night (6/13) I’ll be sharing the stage and swapping songs with the incredibly talented Rosalba Valdez at Black Dog Vinyl Cafe in Plainfield, IL. Don’t miss this one! #music #livemusic #songwriter #originalmusic

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Jason Benefield @jasonbenefield.com · 08/06/2026

Thanks for all the kind words about “Rich Man.” If you haven’t heard it yet, go give it a listen! #music #songwriter #protestsong

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Jason Benefield @jasonbenefield.com · 06/06/2026

Mona wants you to go stream “Rich Man” on your favorite streaming service. She told me. Then she fell asleep. #dog #originalsong #songwriter #spotify #applemusic

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Jason Benefield @jasonbenefield.com · 05/06/2026

“Rich Man” is out everywhere. Stream it and share it. Art is political. Say the things you need to say and don’t let anybody tell you to “shut up and sing.” We need your voice and you are not alone. Oh say can you see?

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Jason Benefield @jasonbenefield.com · 04/06/2026

“Rich Man” is coming tomorrow, 6/5 (or it might already be out if you’re reading this from the Eastern Hemisphere). Bandcamp might get it this evening, so go find me over there. This is a protest song. Stream it and share it if you dig it. Don’t if you don’t. That’s fine too.

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Jason Benefield @jasonbenefield.com · 03/06/2026

“Rich Man” drops in just a couple days. Stream it everywhere on 6/5. #originalmusic #protestsong #songwriter #acoustic

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Jason Benefield @jasonbenefield.com · 02/06/2026

June is light as far as gigs go, but it’s a case of quality over quantity. 6/13: Song Swap at Black Dog Vinyl Cafe with the marvelous Rosalba Valdez 6/17: solo at Preservation in Geneva 6/27: solo again at MilkStop in La Grange “Rich Man” drops Friday, so go pre-save it.

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Jason Benefield @jasonbenefield.com · 01/06/2026

Coming 6/5. Pre-save here: distrokid.com/hyperfollow/...

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Jason Benefield @jasonbenefield.com · 01/06/2026

Happy Pride, my friends. Wishing you love, respect, and acceptance. Don’t let the bastards get you down. I got your back ❤️

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Jason Benefield @jasonbenefield.com · 31/05/2026

I love getting new stickers from @stickerjunkie.bsky.social. If you need great stickers with a quick turnaround hit them up. They’re the absolute best. Also, if you haven’t heard, my new single“Rich Man” will be streaming everywhere this coming 6/5. Head to my website for the pre-save link.

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Jason Benefield @jasonbenefield.com · 29/05/2026

My new single “Rich Man” is coming on June 5th. I recorded and mixed this on my iPhone using a Shure MV88 and GarageBand. It’s raw and imperfect and real and everything AI isn’t. I hope you dig it, but I know some folks won’t. That’s ok. I said what I needed to say.

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Jason Benefield @jasonbenefield.com · 28/05/2026

Oh say can you see? Streaming everywhere 6/5

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Jason Benefield @jasonbenefield.com · 27/05/2026

If you’re ever in Chicago (or the collar counties) let me know. If you’re not, go listen to Chicago Song on the streaming service of your choice. Next best thing.

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Jason Benefield @jasonbenefield.com · 26/05/2026

My next Song Swap at Black Dog Vinyl Cafe is happening on 6/13, and I’m beyond excited to welcome the magnificent Rosalba Valdez as my very special guest. Mark your calendars and come support live, original music.

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Jason Benefield @jasonbenefield.com · 22/05/2026

For my fellow fingerstyle guitar nerds: Travis picking the verse chords of “Poets and Prophets” on my new Martin GPE Inception. Got some annotations in there, too.

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Jason Benefield @jasonbenefield.com · 21/05/2026

Don’t scroll by without saying “hi” to Mona and telling her how good of a girl she is or so help me…

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