Abundance of gigs all part of Will Dailey’s plan for 2021
Earlier this summer, someone booked Boston singer-songwriter-DIY-champ Will Dailey to play a private show on an island off the Cape.
“They took me out to this island with about 30 boats in the water and I played on this bluff out to the boats,” Dailey said ahead of his gig at, well, he’s got upcoming gigs everywhere.
Dailey can’t even say if that will be the most curious show he’ll play in 2021. A few months back, he stated he wanted to play 100 events before 2022. He’s racked up 31 with a score more on the books, including house concerts, a dance studio in Ipswich, a mini festival in Vermont, a major festival in California and Boston’s City Winery on July 22.
“My first show back was in March when my friend from Northeastern called and said, ‘Want to come play guitar outside with a mask on?’” he said. “I’ve played a dozen backyards already. I’ve played 10 bars, and I mean playing three sets in the back corner while everyone drinks, something I haven’t done in years. I wanted to go back to every footprint I’ve made and stand in it again.”
With his career a few years shy of 20, Dailey has seen a lot: indie success, major label hype and fallout, indie success again, and constant touring across the States, Europe and elsewhere. But, like everyone else, the pandemic drove his art and livelihood into a ditch. Days after the clubs shuttered in March 2020, Dailey rallied with a livestream series called the Isolation Tour and raised thousands of dollars for the staff at local venues from Great Scott to Toad to Atwood’s (some of which have yet to reopen or have closed for good).
“With live streaming, it felt good to connect, it felt good to play music, but then you close your laptop and the most important part, the human exchange that happens in person, is missing,” he said.
So, to make art and money and human connections, Dailey set his sights on 100 shows. It’s goal he calls, in a word, “stupid.”
“Here’s the thing, I’m kind of realizing I won’t make it,” he said with a laugh. “I’ve had two cancellations because of rain, and I can’t rebook them because I’m so booked. But it just seemed like something I wanted to strive for more than something I wanted to do. I want to go everywhere and be with people in every kind of live scenario.”
After the major label detour, he has become an artist who thrives on visceral interactions. He plays a ton of fundraisers, collaborates with artists across genres and produces lots of New England acts. He has also reached people thousands of miles from here on solo, duo, trio or fullband tours.
“On behalf of all artists, especially those in America, I will say that if you are dedicated to doing this for life, you are never on solid ground,” he said.
But that worry tends to recede when you’re busy, productive and getting audiences to sing along with every word. If that’s at a hundred shows or 73 or 10, it’s all a thrill.
“A couple weeks ago, I had my first string of five nights in a row (in 2021) and I collapsed at the end,” Dailey said with a laugh. “Sometimes you just want to exhaust yourself until you collapse.
“So when I collapse in December after hopefully playing a few nights (in Davis Square) at the Burren, after playing with Pearl Jam at a festival, at Danny Clinch’s gallery, with KT Tunstall, and whatever else comes down the pike, I hope I feel healed.”
Details and tickets to Will Dailey’s City Winery show and plenty of others at willdailey.com.