You don't become a world renowned songwriter without exploring grief and loss in your lyrics from time to time, and Freedy Johnston is as well-versed in those areas as any of his peers.
Freedy this year released his ninth studio album, Back on the Road to You, and promoted it with the lead single, "Darlin'," featuring Aimee Mann, which is by his own admission one of the saddest song he's ever recorded.
"It's just a simple song ... it's a very depressing song about a couple that are mourning — there's not enough information in the song to know all this — but they're mourning their child who's died, and implication is through a drug-related suicide thing, and that's the song," Freedy explains.
But Aimee did more than just add her background vocals to the song; she also provided the illustrations used in the music video.
"When I talked to her about the song, she really responded to the content and did a series of drawing, illustrating the story of the song and expanding on it really. And then an editor made a cross-faded video of those drawings and fades in and out the lyrics. It's really highly emotional. I watched it one time, I burst into tears, like 'I can't watch that. It's too sad.'"
While Freedy can't watch his own music video, he had no qualms about performing the song for Out of the Box live in studio. You can watch Part 1 of his conversation with Clarke via the player above.
Watch Part 2 via the player below, where Freedy looks back on his biggest hit, "Bad Reputation," and making the music video in New York City.
Watch the official video for "Darlin'" via the player below: