From Alanis Morissette to Judy Garland, Jessica Keenan Wynn On the Five Albums That Rocked My World

Last updated September 29th, 2015 by Jessica Keenan Wynn
From Alanis Morissette to Judy Garland, Jessica Keenan Wynn…

Cali girl Jessica Keenan Wynn came to NYC and took us all by storm with her knockout performance as the fierce but evil Heather Chandler in the cult musical Heathers.

Soon she found herself starring as Cynthia Weil in the blockbuster Broadway show Beautiful.

Now, on October 5, she makes her Feinstein’s/54 Below debut with a new show inspired by her West Coast roots.

Below, Jessica Keenan Wynn recalls the five albums (all by kick-ass female artists) that rocked her world and influenced her.

Alanis Morissette—Jagged Little Pill Why I Chose It: What precocious, grungy, plaid donning, Doc Martin stomping girl in the ‘90s didn’t love and praise this album?! I was in grade school singing lyrics I didn’t care to understand, but melodies I yearned to tackle, mostly in my best friend’s bedroom with her poster hanging over the bed frame. A comical religious practice of sorts; singing to our muse. “You Oughta Know,” “Hand In My Pocket,” “You Learn,” and “Ironic” are just a few that I could most likely sing to perfectly, even though I haven’t heard them in years and years. Alanis was my introduction to a new type of female badassery I had never heard of. I was hooked.

Year I Discovered It: 1995—in 5th grade, trying so hard to be an angsty elementary scholar.

Ultimate track: “Head Over Feet”

Judy Garland—The Complete Decca Masters Collection Why I Chose It: This was the first CD set that I listened to non-stop for years. It ranges in 4 discs from “The Jitterbug,” a song cut from Wizard of Oz, to her earliest track “Dear Mr. Gable: You Made Me Love You,” to every song from my favorite movie, Meet Me In St. Louis. Judy was my first love. I had vintage Judy paper-doll books, tons of bios devoted to her in my shelf, and a selection of MGM glamour shots on my wall (next to my Hanson poster, of course). This woman shaped my love for standards, storytelling through song, and finding the balance between sweet and sassy. I love Judy, don’t you?

Year I Discovered It: 1994—elementary school. Played it on repeat with my 6-disc CD and cassette player, that was the size of a mini fridge.

Ultimate track: “Zing! Went The Strings of My Heart”

TLC—CrazySexyCool Why I Chose It: Because I had no idea what “creeping” was when I was singing along to track 2 at 8 years old, nor had I ever seen a “Waterfall”, but knew exactly how to mime all the bodies of water mentioned. It’s just so ridiculously funny in hindsight. I LOVED this album, which includes some of the most mature material a child could sing along to. Nonetheless, Mom let me live my life and create a lyrical dance routine to “Red Light Special.” I thought it had to do with my red hair…

Year I Discovered It: 1994 driving with my best friend at the time to Disneyland. She had a really cool Mom…

Ultimate track: “Diggin’ On You”

Sara Bareilles— Little Voice 2009 Why I Chose It: Sara Bareilles is one of the most important voices for this generation. She is authenticity personified. Her songs are penned beautifully with vibrancy, audacity, fragility, and freakin’ fun. I have adored and studied every album of hers. She can write a song like “Sweet As Whole” and then bust out “City” in one breath. AND NOW SHE’S A BROADWAY COMPOSER? Dreams, goals, squad, ALL THE HASTAGS! I am a forever fan of this insanely talented woman.

Year I Discovered It: 2009—senior year of college at UCLA. I never wanted to go to “Vegas” more.

Ultimate track: “Between the Lines”

Jane Monheit—Come Dream With Me Why I Chose It: This album consumed me. I was about to graduate high school and dive into studying theatre. My aunt and uncle had given me her album after a benefit they went to, where she was performing. I put the album into my CD player, and I was hooked within 30 seconds. Her version of “Over The Rainbow” begins acapella and isn't joined by piano for 30 seconds. This opening reveals this simple, supple, spellbinding voice that she is known for. Her covers introduced me to Bread’s “If,” Joni Mitchell’s “A Case of You,” and Antônio Carlos Jobim’s “Waters of March.” I was a lesson in music history! Judy Garland was my idol growing up, as mentioned earlier, followed by Barbra, and then along came Jane. To this day, her album and another titled, “Taking A Chance On Love” are two I repeatedly revisit month after month for a pick me up. Also, I didn’t even realize my top 5 were all women, until now. YAS, ladies!

Year I Discovered It: 2002—senior year of High School, driving around in my VW Jetta and dreaming of a Broadway stage with Jane’s jazzy, vocal coloring.

Ultimate track: “Waters of March”

See Jessica Keenan Wynn take the stage at Feinstein's/54 Below on October 5, and check her out eight times a week on Broadway in Beautiful.