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Nolan Feeney
October 19, 2017 AT 11:25 AM EDT

When Tegan and Sara’s Sara Quin looks back on the band’s 2007 album The Con, which took their career to a new level of mainstream success, she remembers the dread of that era: loved ones passed away, she went through a divorce, their label folded — and much of that turmoil showed up in the music. “I listen back to the songs and wish I could get in a time machine and go back and hug myself,” Quin tells EW. But now there’s a reason to look back and celebrate: The Con X: Covers, a 10th-anniversary tribute album (out Oct. 20) that reimagines the group’s seminal LP with covers from Ryan Adams, Paramore’s Hayley Williams, Bleachers, CHVRCHES, and more. The project also coincides with The Con X: Tour, which kicks off the same day the album comes out and will feature stripped-down arrangements of every track from The Con in addition to other songs from the band’s extensive catalog. Below, Quin and some famous friends — Cyndi Lauper, Ryan Adams, and Sara Bareilles — share how the new album came together.

Hidden Drama

While The Con features some of Tegan and Sara’s darkest, most gut-wrenching lyrical content to date, Quin says she and her twin sister pursued upbeat arrangements and production to keep the 2007 album from feeling like “a f—ing funeral march.” Many of the tracks on The Con X: Covers unearthed that gloom. “When I really examined the lyrics, it was so beautiful and sad,” Sara Bareilles says of her version of “Floorplan.” “I decided to use the ache of the sentiment to redirect the soundscape. I played it on my out-of-tune piano, added some programming and spooky backgrounds, and it all came together in less than 24 hours.” The renditions gave Tegan and Sara new entry points into their own work. “There’s anguish in [Bareilles’] version of ‘Floorplan’ that is maybe missing from mine on the record,” Quin says. “Not that I want to tear our versions apart! But it was nice to have these artists push into the emotional core even more.”

Giving Back

Tegan and Sara, both 37, grew up idolizing Cyndi Lauper and have covered multiple songs from her catalog throughout their career. Quin describes hearing Lauper’s dancey take on “Back in Your Head,” one of the project’s digital bonus tracks, as “totally surreal.” Says Quin, “It’s fascinating when someone you’ve listened to since you were 4 sings your song.” But Lauper was more than happy to lend a hand for the project, whose proceeds will go to the Tegan and Sara Foundation benefiting LGBTQ women. “I love those girls,” Lauper tells EW. In 2008, she handpicked the duo to join her True Colors tour, which supported the Human Rights Campaign and other organizations; the success of the tour inspired Lauper to start the True Colors Fund, which aids homeless LGBTQ youth. “Tegan and Sara were there to help me when I was starting my foundation, and I thought it was quite apropos that I support them on this record as they launch theirs,” Lauper says.

Rocking Out

After spending the first decade of their career toiling in the indie-rock world, Tegan and Sara have spent the past few years transitioning to a more pop-oriented, keyboard-based sound. And while Quin jokes that she’s totally over the guitar (“Tegan is so annoyed at me; we’ve been doing rehearsals for [The Con anniversary] tour, and I am not playing any guitar”), one artist — Ryan Adams — made her reconsider. Adams, who also covered “Back in Your Head,” gave the song a supercharged, ax-heavy makeover. “When I heard that, I was like, ‘Oh, I think I want to make a rock record again,'” Quin explains. Adams’ involvement was also special given his early support of the band: He took them on tour in 2002 and covered them back in the day. “I look up to them, actually,” Adams tells EW. “Although not in person, as they are maybe the only people shorter than me in music.”

Building a Legacy

In addition to tracks from their musical heroes (Lauper, Adams) and peers they came up with in the industry (Bleachers, Paramore’s Hayley Williams), The Con X: Covers also features contributions from artists who count Tegan and Sara as major influence and inspiration: Shura, MUNA, Shamir. “Tegan and I have made a massive effort over the last 10 years to create a community that we didn’t feel we had in the first 10 years of our career,” Quin explains. “Some of it is just, ‘Hey, I saw you put a record out, you’re young and this industry can be crazy, here’s my number, call me anytime. In a way this record is an extension of that … Some of these bands are people I hope would count on us if they needed something.”

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