Folk-pop artist Mason Jennings celebrates his 25th anniversary at City Winery in DC

Hear our full conversation on my podcast “Beyond the Fame.”

WTOP's Jason Fraley previews Mason Jennings at City Winery (Part 1)

For a quarter century, folk-pop fans have enjoyed the songwriting gold of Mason Jennings.

He celebrates his 25th anniversary by coming to City Winery in D.C. on Sunday, Aug. 21.

“I love that venue,” Jennings told WTOP. “It’ll just be me with a guitar and grand piano. I’ll be telling stories about the songs and playing stuff from all the records in a very intimate setting. … It’s a really cool venue to hear the essence of these songs. … There will probably be four or five new ones, but I try to sprinkle stuff in from all of my albums.”

Born in Hawaii in 1975, Jennings moved to Pittsburgh and learned to play guitar at the age of 13 before dropping out of school and moving to Minneapolis to pursue a music career.

“I was only 22,” Jennings said. “I went to an artist counselor with a backpack of cassettes. He was like, ‘Dude, you’ve gotta get it together and make a CD.’ … I had a little duplex, got a reel-to-reel four-track machine and made this … eight-song CD. … I recorded all of the instruments myself in my wooden living room and layered drums, bass and guitar.”

The result was his self-titled debut album, “Mason Jennings” (1997), which called “an amazingly realized work. A distinct sound and vocal style is evident, and there’s not one clunker on this entire disc.” Truer words have never been written thanks to gems like “Nothing,” “Butterfly,” “California,” “Big Sur” and “Darkness Between the Fireflies.”

“I tried to get a record deal, but at that point nobody was interested, so I just started selling them,” Jennings said. “We sold like 100,000 of those CDs, so I said, ‘Well, I guess I can do it myself and go directly to the people,’ so it was sort of a DIY and it sort of surprised me. … It’s held up well over all these years. It’s been kind of a cool little boat on the waters.”

The New York Times noted Dave Matthews vibes in his second album, “Birds Flying Away” (2000), but it also featured ’60s-style protest songs with “United States Global Empire,” “Dr. King” and “Black Panther,” singing, “Think of the dead in Vietnam, think of the dead in Birmingham, think of the freedom we don’t understand, asleep in a bed in a stolen land.”

“I was reading Huey P. Newton and Eldridge Cleaver, Black Panther stuff, and it just got inside the songs,” Jennings said. “Whatever I’m doing at the time or interested in usually ends up in song in some form, so that record, I guess I was reading a lot of that stuff at the time. … I’m a huge reggae fan, so that sneaks in there throughout the discography.”

His third album, “Century Spring” (2000), featured tearjerkers like “Adrian” and clever turns of phrases like “Sorry Signs on Cash Machines,” inspiring to call Jennings “an accomplished pop troubadour yearning for romance” who will likely inspire listeners to “push the replay button to squeeze every ounce of charm from this enticing collection.”

“I was definitely moving to piano music because the first two records don’t have any piano,” Jennings said. “I got a piano, so ‘Sorry Signs’ was kind of like, I wrote that on a piano and, yeah I don’t know, I was just looking toward some hope. Sometimes you’re playing those chords, and there’s something inside of it that just felt like a hopeful song.”

His fourth album, “Simple Life” (2002), was a stripped-down acoustic set recorded in his friend’s living room on a two-track tape recorder. “Executed magnificently in a casual environment, it surely ranks among Mason Jennings’ finest work,” wrote

He followed up with “Use Your Voice” (2004), hailed by for “quiet dignity, humorous grace, and elegant craft.” It includes “The Light (Part II),” giving perspective on life changes; “Lemon Grove Avenue,” humming a ditty to set up poetic lyrics of pastoral imagery; and “Keepin’ it Real,” an upbeat vibe with a catchy hook: “Oh yes, my oh my.”

“‘Keeping’ it Real’ was actually for ‘Shrek,'” Jennings said. “‘The Light (Part II)’ was supposed to be on my first record. … You get hung up on the physical, but everything regenerates. … Then I was driving through San Diego and saw a Lemon Grove Avenue sign. … One guy goes, ‘Have you actually been to that avenue? It’s not a cool place.'”

American Songwriter called his sixth album, “Boneclouds” (2006), the “most dynamic and richly textured album” of his career, featuring the haunting “Jackson Square,” the romantic “If You Ain’t Got Love” and the live-in-the-moment masterpiece “Be Here Now,” boasting some serious ring tone potential with the refrain, “Sun comes up, and we start again.”

“I was meditating a bunch and trying to learn because I had so much anxiety,” Jennings said. “I heard somebody say that everything in the past and future only happens in the present moment. I thought about that for weeks and realized there really is no access point to the past or future except for the present moment. … That song came out of that idea.”

Fittingly, Jennings signed with Jack Johnson’s Brushfire Records for “In the Ever” (2008), featuring “Something About Your Love,” “I Love You and Buddha Too,” “Fighter Girl” and “Your New Man,” which plays like a revenge song mixed with a stand-up comedy routine.

“I was listening to ‘Folsom Prison [Blues]’ by Johnny Cash; he was always cracking people up,” Jennings said. “I was dealing with stressful stuff [and] I was going to The Troubadour in L.A., so I was like, ‘Maybe I’ll try this song for the first time like a stand-up comedian.’ … I just sang it and recorded it, so you’re hearing the first crowd reaction in real time.”

Over the next decade, Jennings consistently cranked out albums for his most hardcore fans, including “Blood of Man” (2009), “The Flood” (2010), “Minnesota” (2011), “Always Been” (2013), “Wild Dark Metal” (2016) and “Songs From When We Met” (2018).

“They’re all different,” Jennings said. “‘Blood of Man’ is really low-fi, I did that in the woods, it’s very rock, a lot of songs a very dark. Same with ‘Wild Dark Metal,’ which is a rock record but in a studio, so it’s way more hi-fi. If you want to hear rock, those are the two records to listen to, but a folk record like ‘The Flood’ is just me and an acoustic guitar.”

In 2020, he released “Painted Shield” (2020) with his eponymous supergroup featuring a Pearl Jam alum that reunited with Jennings for his newest album “Real Heart” (2022).

“It was produced by Stone Gossard from Pearl Jam,” Jennings said. “It was a very folk-based record. You’d think it might be rock with him producing, but I recorded a lot of the acoustic guitars and vocals at my house in Minnesota overlooking a lake. It became a rural-sounding, folky record, then Stone and friends added strings and orchestration.”

Over the pandemic, he turned to Facebook livestream events as more than 8,300 people watched him perform his entire debut album, pausing in between acoustic songs to share candid insights about his songwriting inspiration and fun details of his personal life.

“It was awesome for me because I could really get comfortable in my living room and just tell the stories,” Jennings said. “On stage sometimes if you talk too long, people will get restless, but on video, you can tell the whole story and not really feel that, so that was fun. Also, I could do show-and-tell with stuff, show some of the tapes and artwork.”

He’s also a recent father with his three-month-old named Western Jennings.

“I’ve got a 19-year-old and a 16-year-old from another marriage, then I’ve got a newborn now, so I’ve got a full deck — and two step kids, too,” Jennings said. “More love.”

In the end, the key is being open to sparks of creative inspiration.

“I just follow the song,” Jennings said. “It goes where it goes.”

WTOP's Jason Fraley previews Mason Jennings at City Winery (Part 2)

Hear our full conversation on my podcast “Beyond the Fame.”

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Jason Fraley

Hailed by The Washington Post for “his savantlike ability to name every Best Picture winner in history," Jason Fraley began at WTOP as Morning Drive Writer in 2008, film critic in 2011 and Entertainment Editor in 2014, providing daily arts coverage on-air and online.

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