Saturday, September 20, 2025

Song Spotlight: Bennett Woolsey's Tightrope (a night at Hotel Ziggy)

Bennett Woolsey took to the stage at the WFNM  showcase at Hotel Ziggy. A couple years had passed since I last saw one of his sets. That 2023 set was also at Hotel Ziggy and playing that night was former American Idol Maryjo. Anyways, the two are tight friends with Woolsey recently releasing "Used To You" that features Maryjo. 

Bennett Woolsey at Hotel Ziggy
Bennett Woolsey at Hotel Ziggy

On this particular night of music, Maryjo popped on by to sing the song live. It is a match made in heaven with Woolsey's folk vocals being countered with Maryjo's smokey vocals. It is also an interesting personality mix. Maryjo has a very outgoing personality while Woolsey is on the reserved side. It is a  song about a relationship where the two individuals are just not on the same page. 

I laugh,
She cries.
She bites,
I grin. 
Bennett Woolsey at Hotel Ziggy
Bennett Woolsey at Hotel Ziggy

Doing my Internet research, Woosley used to be in a Dallas based band called Brookside. At some point, perhaps in 2023, he moved to Los Angeles to launch a solo career. It was a good move on his part as per a Brookside Instagram post, he recently signed a record label deal. 

What really struck me about the set was his Bob Dylan vibes with a Texas accent. With scuffed boots and pant legs that were frayed, he presents as a singer with a guitar slung around his shoulder, walking down an empty road to hit up a bar's open mic night. 

He ended the set with "Jimmy the Chameleon" which was written during his high school days with Brookside. The packed crowd shouted out "Jimmy Jimmy Jimmy." 

Bennett Woolsey at Hotel Ziggy
Bennett Woolsey at Hotel Ziggy

The song spotlight goes to "Tightrope," which was his upcoming release at the time. "It's a big track. It's very pop, which is great, but it's a little outside my comfort zone of sad acoustic songs." Other than having Maryjo join him for a song, his set was solo acoustic and so he also sang an acoustic version of this song, as well.

Walking with my eyes closed.
High up on a tightrope 
I just keep on moving to the sound of your voice.
   
A song that will no doubt have girls swooning soon.

Partial Setlist: Used To You, Tightrope, Jimmy the Chameleon.

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