"If you're not sad you're not paying very much attention."

Donovan Woods has a talent for writing songs that feel like “real life”: Funny and sad at the same time, plain spoken and poetic in the same breath, nostalgic and hopeful at once. As he says, "Two opposing ideas can be true at the same time." 

So it’s no surprise that he named his latest album Both Ways.

He says that when he thinks about it, there’s just “so much sadness”. He says that he loves to watch an audience turn to mush, to make them feel comfortable and then slowly deliver the tragic sense of life. He says he does it by using “tricks of language” that feel familiar and colloquial. He says he developed his confessional style of songwriting, which is generally considered to be country or folk, by listening to hip hop as a kid growing up in Sarnia, Ontario.

There’s a lot about Donovan Woods that makes him an outsider to the Nashville singer songwriter circles in which he often travels, but there’s plenty that puts him right at home there. Particularly, a devotion to highly personal, narrative writing.

Despite all the tragedy, I think he’s also one of the funniest writers around. Listening to his music, one is constantly toggling between tears of laughter and tears of sadness. At least I am. And talking to Donovan Woods is similar. He’s very a pleasant guy, easy going, down to earth and funny. Sad funny, sure. Bitter funny. Excruciating funny. But funny all the same. 

Although his songs are custom made to be performed by him (“people say I sound like I’m singing right in their ear”) they have also been recorded by stars like Tim McGraw and Charles Kelley (of Lady Antebellum).

Donovan came to the Third Story headquarters recently during a run of shows and promotion for his new album. Here he talks about writing songs that feel like real life, the big scam of success (“by the time you get the thing you always wanted, you feel like you deserve it”), how to make it in Nashville, and why Wisconsin is the state most like Canada.

This episode features an introduction by me in conversation with my wife, Amanda.

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