Jill Sobule vs. Katy Perry | Head 2 Head

In the 14th edition of Head 2 Head (2025), Jill Sobule and Katy Perry contend for the best “I Kissed a Girl.”

Welcome to Head 2 Head! Most of the time, on Head 2 Head, we pit at least two musicians performing the same song and compare their performances.  After deliberation, we decide which performance is the best or moves us more subjectively.  In the 14^th edition of Head 2 Head (2025), Jill Sobule and Katy Perry contend for the best “I Kissed a Girl” – two different songs with the same title and similar themes. So, without further ado, let the Head 2 Head commence!

1. Jill Sobule, “I Kissed a Girl”

Jill Sobule // Atlantic Recording Corporation // 1995

“So, we laughed, compared notes / We had a drink, we had a smoke / She took off her overcoat…” Okay, so, what happened next, Jill Sobule? Why, “I Kissed a Girl”, of course! “I Kissed a Girl” is the seventh track from the deceased () musician’s 1995 self-titled album. What did she and her friend, Jenny, compare notes about? Their questionable boyfriends include Brad, who is “dumb as a box of hammers,” and Larry, whom Jill believes, “I think I can do better.” Oh, snap! Sobule wrote the bi-curious/gay gem with Robin Eaton.  Brad Jones and Eaton produced it.  “Kissed” impacted the pop charts modestly, peaking at number 67 on the Billboard Hot 100.

“I Kissed a Girl” not only satisfies because of its queerness (“They can have their diamonds / And we’ll have our pearls” ), but also its musicianship.  The sound is eclectic, with country, folk, pop, and rock sensibilities. The groove is particularly satisfying. There is an awesome, distorted, and mean-sounding guitar solo that appears toward the end of the song.  Sobule delivers beautiful, playful, and tongue-in-cheek vocals. As the song progresses, it sounds like her vocal performance grows even more confident and more dynamic.  Still, it is those queer lyrics that catch our ears. After Jenny tells her boyfriend she’ll be late, she feels guilty, considering, she’s kissing Jill.  “Then I looked at you, you had guilt in your eyes,” Sobule sings in the second verse, expanding on the rendezvous, continuing, “But it only lasted a little while / And then I felt your hand above my knee.” Oh, snap! While Sobule acknowledges kissing “a girl won’t change the world,” she’s glad she did and admits, after kissing a girl for the first time, “Won’t be the last time.” Word. Rest in peace, Jill Sobule.  You left an LGBTQ+ gem for the ages with “I Kissed a Girl”.

Appears in :

• Jill Sobule, I Kissed a Girl: Beaming with Pride 37 (2025)

2. Katy Perry, “I Kissed a Girl”

One of the Boys // Capitol // 2008

“That was never the way I planned / Not my intention / I got so brave, drink in hand / Lost my discretion…” Hmm, that’s very telling, Katy Perry.  Of course, the opening lines from the first verse set up her 2008 bisexual anthem, rather, bi-curious anthem, “I Kissed a Girl.” “I Kissed a Girl” was the lead single from her second studio album, and first of note, One of the Boys. Perry launched her pop career with a bang. The juiciest part of the verse is the second half, where Perry asserts, “Just wanna try you on / I’m curious for you…” Of course, the ‘you’ is another woman. Perry wrote “I Kissed a Girl” with Dr. Luke, Max Martin, and Cathy Dennis. Dr. Luke and benny blanco produced it. Notably, “I Kissed a Girl” spent seven weeks at number one on the Billboard Hot 100. It was certified multiplatinum by the RIAA.  Perry was nominated for her first Grammy at the 51^st Annual Grammy Awards for Best Female Pop Vocal Performance. She lost the award to Adele, who was soulfully “Chasing Pavements”.

Does “I Kissed A Girl” have a transcendent message? Eh. A Huffington Post article sheds some light on this controversial, though extremely popular hit. Regardless of the controversy, you could argue “I Kissed A Girl” broke barriers at the time.  Same-sex interactions weren’t a popular topic for pop hits back in 2008.  The thing is, Jill Sobule had already kissed a girl long before Perry…13 years before. While both songs have the same title and explore bisexuality, they do sound far different. Also, ask yourself the question regarding “I Kissed a Girl”: Did you not “like it” at the time? Are you not entertained! The chorus is the section to beat:  

“I kissed a girl, and I liked it
The taste of her cherry ChapStick
I kissed a girl just to try it
I hope my boyfriend don’t mind it
It felt so wrong, it felt so right
Don’t mean I’m in love tonight
I kissed a girl, and I liked it
I liked it.”

The “cherry ChapStick reference” was naughtier than anyone thought (female private parts ). Jill Sobule didn’t take it that far…

Appears in :

• 12 Interesting Songs That Reference Bisexuality (2020) 
• A Compendium Comprised of 100 Notable LGBTQ+ Songs (2020)

The Verdict  

Which “I Kissed A Girl” is the best? Is it the original gay anthem by the late Jill Sobule or the 2008 breakout pop song by Katy Perry? It is worth mentioning that Sobule wasn’t thrilled about Perry’s same-sex song – she had some choice words ! Perry’s record was a huge pop success.  It was catchy to the nth degree. It put Katy Perry on the map. Also, at the time, it did break barriers.  But, again, Sobule broke the barrier first – 13 years earlier.  No, it didn’t earn the degree of success of Perry’s bop, but, in my humble opinion, it’s the best of the two songs.  So, in this battle of two different songs that explore bisexuality, Jill Sobule gets the edge.  R.I.P., Jill.

Jill Sobule vs. Katy Perry: Head 2 Head No. 14 (2025) [: Brent Faulkner / The Musical Hype; Atlantic Recording Corporation; Capitol; Israel Torres, KoolShooters, Los Muertos Crew, RDNE Stock project, Thomas Ronveaux from Pexels]