Boston quintet Lake Street Dive has been ‘Good Together’ for more than two decades

Twenty years ago, Bridget Kearney’s song “Sometimes When I’m Drunk and You’re Wearing My Favorite Shirt” won in the jazz category of the John Lennon Songwriting Contest.

The bassist used the $1,000 prize money to fund an album for her band Lake Street Dive, which she’d co-founded the previous year in Boston with four fellow New England Conservatory of Music students. And two decades, seven more albums and one major personal change later, Kearney still considers it a worthwhile investment.

“I was pretty young and didn’t really have any disposable income, so it was nice to do something meaningful with (the money),” says Kearney, 40. “I didn’t want to fritter it away on lattes and whatever else. It was great to have that album (‘In This Episode...’) under our belts as the consummation of