In our bid to love and to be loved, we may experience heartbreaking loss, as orchestrated by an omnipresent force and sealed in our fate before we were even born. If we are one of the lucky few, we may be struck by Cupid ⎯⎯ but it often comes at a price. Virginia singer, songwriter and guitarist Thorp Jenson, who is set to release his self-produced debut album Odessa later this year, finds solace in the music. From The Band and Bruce Springsteen to modern-day troubadour Sturgill Simpson, Waylon Jennings and Merle Haggard, he immersed himself in some of the greatest work of the American songbook to reflect upon his own journey and his place among the stars. Compiling his favorites, he has shared a playlist called Songs of Love & Loss, exclusively to B-Sides & Badlands.

You’ll find plenty of other recognizable names, including Neil Young (who kicks off the lineup with “Out on the Weekend”), Marvin Gaye, Townes Van Zandt and Tom Petty. As the summer waxes on ⎯⎯ and fleeting romance reaches a fevered pitch ⎯⎯ the playlist is a must-listen for any music fan, regardless of musical preferences.

Below, Jenson also breaks down each inclusion, detailing his personal connections and the vast cultural significances carried with a slew of the most prolific songwriters ever.

Odessa (out Oct. 20) boasts a wealth of the finest players in all of music. Those include: Cameron Ralston (Foxygen, Matthew E. White), Suzi Fischer (Foxygen) and Andrew Randazzo (Natalie Prass).

“Out On The Weekend,” Neil Young

I love this track for so many reasons. Somehow, Neil seems to deal with life and love with both sadness and joy wrapped in together. It has a sort of somber feel and overall sound, but I think if you unwrap his lyric a bit, you’ll find some joy to it all in there. Sonically speaking, it is also one of my favorite snare sounds of all time.

“Don’t Do It,” The Band

From Rock Of Ages. Admittedly, I got hip to this song from the last waltz even though it’s really a Marvin Gaye song. I do love Marvin’s version but you have to love The Band’s version. Allen Toussaint’s horn arrangements are killer, and Levon really lays it down both in the drums and on the vocals, and the rest of the cats in The Band are bringing it, too.

“The River,” Bruce Springsteen

The boss has a pretty uncanny ability to tell a story through someone else’s lens. I think he is kind of telling his sister’s story through the lens of his brother in-law. It is a pretty powerful one to let wash over you.

“Turtles All The Way Down,” Sturgill Simpson

This song has everything you need: Jesus, Buddha, solid amount of drug references… But really, I think Sturgill is talking about universal love. And it’s Dave Cobb’s production that is a big inspiration for me.

“Today I Started Loving You Again,” Merle Haggard

I just think this is such a perfectly written song. I love the line “with only these few million tears I’ve cried.” Merle’s delivery is incredible. C’mon, are you kidding me? It hits me every time.

“Dreaming My Dreams with You,” Waylon Jennings

Waylon said this was the greatest song he ever sang in his career. I remember seeing a documentary where he talked about how he’d been married several times, but that once you love someone, it stays with you forever even after you’ve moved on, and that’s why he could relate so much to the song.

“You’re A Big Girl Now,” Bob Dylan

Blood on the Tracks was probably the first singer/songwriter album I latched onto. Bob tells his story of moving on from love so eloquently on this song and seems to also deal with loving someone despite moving on.

“Only A Fool Breaks His Own Heart,” Nick Lowe

Nick Lowe’s album The Convincer is a real sleeper, folks. You should go get it right now! The whole thing is incredible. Nick tells the story of moving on past love on this track but does it in a way only he can do, never taking himself too seriously. Side note: I’m pretty sure “Lately I’ve Let Things Slide,” the next track on the record, could have made the Big Lebowski soundtrack if it had come out two years earlier.

“I Met A Little Girl,” Marvin Gaye

From Marvin’s album Here My Dear. The story on the album is that Marvin had to give all of the money from his next album to his ex-wife as alimony, hence the title. He really serves it up and tells their story from a pretty raw wound on this track and really the whole record. He does not hold back. About 3:20 in and forward is my favorite part, “Cry, cry, cry, do you cry about me?” Whoooo that delivery! Wow. Also, the synth solo is killer.

“So In Love,” Curtis Mayfield

Curtis might be my favorite songwriter of all time, and this is a perfect love song. Also, the horn arrangement on this track reminds me of Richmond. We have a cool tradition of horns in this town, and it sounds like something the cats around here would play.

“No Place To Fall,” Townes Van Zandt

What a beautiful song from Townes’ Flying Shoes. I love the line, “I ain’t much of a lover its true, I’m here then I’m gone and forever blue.” I love his honesty in that line; it’s powerful.

“Wake Up Time,” Tom Petty

I’ve said before how I think this whole record is perfect, but it is easy not to make it to the very end especially with our short attention spans these days. This song ends the album, and I think it is a good way to end this playlist… “It’s wake up time, time to open your eyes, and rise, and shine.”

Photo credit: Melissa Brugh

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