Nancy Sinatra vs. Jessica Simpson | Head 2 Head 🗣️

On the 18^th edition of Head 2 Head, Nancy Sinatra & Jessica Simpson duke it over respective takes on “These Boots Are Made for Walkin’.”

Welcome to Head 2 Head! On Head 2 Head, we pit at least two musicians singing the same song together, comparing and contrasting their performances.  Then, after much deliberation, we deliver a verdict of which performance was the best, or at least, subjectively, which performance moved us more.  For our 18^th head-to-head, Nancy Sinatra and Jessica Simpson ‘duke it out,’ going head-to-head over respective takes on “These Boots Are Made for Walkin’.” So, without further ado, let the Head 2 Head commence!

1. Nancy Sinatra, “These Boots Are Made for Walkin’”

💿 Boots • 🏷 Boots Enterprises Inc. • 📅 1966

“Are you ready, boots? Start walking!” Nancy Sinatra is the daughter of an iconic musician, Frank Sinatra. Furthermore, she’s a musician herself, among many other accomplishments and accolades.  As a musician, Nancy is renowned for one song in particular: “These Boots Are Made for Walkin’.” The classic appears on her 1966 album, Boots.

“These Boots Are Made for Walkin’” is a prime example of a novelty song.  It’s that ‘once in a lifetime’ number that’s cutesy, corny, and schmaltzy, yet incredibly irresistible.  Sinatra is even playful in her vocal performance, amplifying the tongue-n-cheek sensibilities.  “You been messing where you shouldn’t have been messing,” she sings on the first verse, continuing, “And now someone else is getting all your best.” Those vibes continue as the song progresses, with Sinatra asserting on the second verse, “You keep same-ing when you ought to be changing.” It’s far more violent on the third verse, where “I’ve just found me a brand-new box of matches, yeah / And what he knows you ain’t had time to learn.”  Of course, the crème de la crème – the crowning achievement – is the chorus where:

“These boots are made for walking
And that’s just what they’ll do
One of these days these boots
Are gonna walk all over you.”

Appears in 🔻:  

• 13 Songs That Totally Have It MADE (2021)

2. Jessica Simpson, “These Boots Are Made for Walkin’”

💿 The Dukes of Hazzard (Music from the Motion Picture) • 🏷 Columbia • 📅 2005

“Are you ready boots / Start walkin’!” Back in the day, Jessica Simpson had a run.  Was Simpson as impactful as Christina Aguilera, Britney Spears, or P!nk? I’d argue NO, but she has gold and platinum singles and albums.  Simpson, of course, cemented her place in pop culture with that questionable reality show with then hubby Nick Lachey (Newlyweds), as well as her cover of “These Boots Are Made for Walkin’”.  What’s most notable regarding the cover of “Boots” is the music video, which is rowdy, titillating, and honestly, just must-see TV. I mean, Willie Nelson guests and hits a man over the head with a beer bottle! Now that’s bad ass!

Of course, the music video isn’t what we’re examining but rather, the song itself.  In Jessica Simpson’s hands, “These Boots Are Made for Walkin’” gets more country-pop flavor (Jimmy Jam and Terry Lewis produce).  Simpson is playful in her vocal performance – cutesy matching the novel nature of the record.  There’s no way you leave this take and feel like you’ve heard a vocal masterclass (no shade intended… well… not that much).  That said, given the fact that “Boots” is novel, Simpson’s exaggerated tongue-n-cheek take is successful.  Notably, Jessica’s version also changes some lyrics and adds some sections including a post-chorus, bridge, and a cool breakdown section:

“Hey y’all
Wanna come and see something? (Uh-uh, uh-uh)
Can’t touch, can I get a hand clap? For the way I work my back
Tick-tock, all around the clock, drop it
Push ya tush, like that
Can I get a suueey? (Suueey)
Can I get a yee-haw? (Yee-haw).”

If nothing else, Simpson and the songwriting and production team ensure this remake adds some original touches.  That’s admirable.

The Verdict 👨🏿‍⚖️

Nancy Sinatra or Jessica Simpson? Sinatra gets the edge.  Her version is the gold standard – definitive to the nth degree.  While the Simpson version is a mix of cringy and fun, give Nancy the flowers she deserves! Case closed!

Nancy Sinatra vs. Jessica Simpson: Head 2 Head 🗣️ No. 18 [📷: Boots Enterprises Inc., Brent Faulkner, Columbia, The Musical Hype, Valentin Tikhonov from Pixabay]