Al Olender Talks Sophomore Album, Alentine’s Day, and Her Return to MilkBoy (2/26)

Al Olender Talks Sophomore Album, Alentine’s Day, and Her Return to MilkBoy (2/26)

As I’m sure you’re aware, this Saturday the majority of the currently partnered portion of the population will be celebrating Valentine’s Day…  However, our dear phriend Al Olender – who we first met in May of 2022, when she dropped her debut LP, Easy Crier – is far more excited about hosting the fourth annual Alentine’s Day this Friday, February 13th, in her current home of Kingston, New York… also home to our phriend Anya Marina, who apparently lives right down the street from Al!

“It’s my favorite thing to talk about!  It’s a community-based show that’s a work and labor of love.  People work on the show for no money.  It’s a spectacle.  It’s not just music, it’s a storyline, vendors, food, projections…,” Olender explains during our most recent phone chat, before going on to proclaim, “It’s Broadway in Kingston, New York!”  For those who can make it to Old Dutch Church in Kingston this Friday (which we would recommend) and want to be prepared for the fourth edition of Alentine’s Day, Al wants to let you know, “The theme is extraterrestrial, so it’s aliens and very spacey…  We’re calling it A Visit To Planet Crush!”

Planet Crush is the official/unofficial setting of Al Olender’s sophomore full-length, The Worrier, which also drops this Friday, February 13th.  The album’s narratives revolve around love of all sorts: past, present, future, fictional, non-fictional, productive, destructive, and everything in-between.  “I’ve gone through a season of growth.  The first album was just me starting out as a musician, but now I’m four years into that,” says Olender when I ask her how she thinks the album compares to Easy Crier.

Olender admits she’s still a bit anxious for the LP to drop, but says she’ll be grateful for any kinds of reactions it receives: “I think there’s a lot of pressure for the sophomore album, even for an artist like me…  I just care if anybody’s listening and if anybody has an opinion at all [laughs].”  However, she tells me that enlisting Nick Kinsey — a familiar face who produced 2023 singles “Almost Famous” and “Runner Up” – to handle production duties at least put her at ease while making the album, which was recorded live to tape, his specialty: “Nick’s a dear friend of mine.  We’ve worked together for a really long time…  Nick is a trusted person who knows me, and he has his hands on the wheel while still letting me be the driver.”

Following Alentine’s Day, Al Olender will kick off a two-month tour on February 25th in her hometown of Baltimore, where she tells me she’ll be giving The 8×10 — a venue where she grew up seeing shows — a proper sendoff before its June 30th closing.  And the following night, February 26th, she’ll be returning to MilkBoy, which has become her regular spot in the 215, which she tells me she’s very excited about it… before admitting that she’s actually very excited for every night on this jaunt.

“I’m so excited to play these shows!  I’m so excited for Philly!  It’s my longest tour ever.  It’s my first shows in Florida, in Deland and Gainesville and Neptune Beach…  I’m really excited for New Orleans, and then the West Coast, Los Angeles and San Francisco, and then Omaha, and Denver, and Minneapolis I’m really excited about, to be able to play music for all of those people at a time like this…  I’m so excited!”

“As always, it’s me and a guitar, Baby!  That’s all you get!” Olender exclaims, laughing, when I ask her what can be expected of the live show.  However, that’s not quite true…  Al is bringing along three of her closest, dearest female friends to provide support for her throughout the dates.  Handling the last third of tour is Aubrey Haddard, who we met in the summer of 2021 and who plays guitar on The Worrier.  Taking the middle third of dates is Ahna Ell, whose 2023 Live at Stop Look Listen was recorded right here in Philly.  And opening the first few weeks of the tour, including MilkBoy, is Philadelphia’s own Abigail Dempsey, a longtime member of Low Cut Connie.  “Abigail’s the best!  She’s coming out of a new nesting period of her life and I’m so excited to hear all of her new music!” says Olender of her buddy.

Not only did Abigail Dempsey open Al’s first-ever show at MilkBoy in 2022, shortly after moving here and just after Al dropped her first album, she also directed the amazing video for “The Cyclone,” the lead single off of The Worrier, which Al tells me came together quite effortlessly: “It was a handheld camera, shot by my best friend, Abigail Dempsey, and we did it at the album cover shoot.  It was one take and I lip-synched along on the first try!”  I tell Al that I love the vibe of the video, which feels very classic NYC, joking, “like Cinema of Transgression… but less X-rated,” to which she quickly replies, “Maybe a little X-rated; my legs are open!”

The last time I spoke with Al Olender was in February of 2023, and when I ask what have been some of the highlights of those last three years, she tells me, “Career-wise, I’ve just had so many incredible opportunities to go on tour opening for amazing artists: Shovels & Rope, John Moreland, Bonny Light Horseman, Gipsy Kings, Deer Tick…”  And I can’t help to point out that, during that very chat, I asked her if there were any artists that she dreamt of touring with and she namedropped both Shovels & Rope and Bonny Light Horseman…  So, for the sake of my dear phriend Al, I have to ask what she’s hoping for 2026…

“I have big dreams!  2026 is gonna be my year.  I want to open a show at Red Rocks.  I want to do a 10-week bus tour with one of my favorite artists.  I want to open for Gregory Alan Isakov, Fruit Bats, Hurray for the Riff Raff, Julia Jacklin, Dean Johnson…  I’m just gonna name it and I’m gonna do it and it’s not stopping!”

*Get your tickets here.

**Listen for an Al Olender classic on the next edition of Philthy Radio, 2/20 (9-11pm ET) on Y-Not Radio.

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