From left: Olivia Rodrigo, Chris Stapleton, Miley Cyrus, Billie Eilish and Jelly Roll are just a handful of artists capable of bringing a classic hit back to life with a remake.

From left: Olivia Rodrigo, Chris Stapleton, Miley Cyrus, Billie Eilish and Jelly Roll are just a handful of artists capable of bringing a classic hit back to life with a remake. (AP photos/Stars and Stripes illustration)

I was on the phone with my dad, predictably dismissing the Grammy Awards ceremony, when he, who had it on his television, said, “Oh, she’s on now.” The “she” he was referring to was Tracy Chapman. Neither one of us was aware that she would be there, let alone performing “Fast Car,” her decades-old hit, alongside Luke Combs, who rejuvenated the song last year, making it a No. 1 single on the country music charts all these years later.

The performance was transfixing. Both of us kind of shut up and just watched/listened. Not only was it touching, but it proved to be my favorite highlight of the night. Chapman looked great, sounded great and was even received in a respectfully great manner by the live crowd. Combs knew the assignment, too, as he seemed happy to play second fiddle to the performance’s biggest star. I keep going back to watch it because if nothing else, those five-and-a-half minutes felt so wholesome.

And yet, as I keep pulling it up on Al Gore’s internet, I find myself asking myself the same question: What could be 2024’s “Fast Car”? Combs’ version climbed up the charts 35 years after the track’s initial release; what current pop star could reach into the depths of the 1989 hit list this year and perhaps cook up some magic of their own? I did some research and here are my entirely unqualified suggestions:

Chris Stapleton: “She Drives Me Crazy”

This could have gone to Nathaniel Rateliff, but we’re talking about bigger pop names here, so Stapleton gets the nod. Plus, the “Tennessee Whiskey” singer doesn’t not have the same vocal inflection Fine Young Cannibals’ Roland Gift displayed on this 1989 hit single. Just imagine this thing slowing down, leaving room for an R&B groove and sparse, tortured vocals from one of country music’s most interesting modern singers.

Lauren Mayberry: “Like A Prayer”

OK, this is only here because she worked it into her solo tour sets last year, and as we all know by now, I’m the biggest Chvrches stan this side of Scotland. Sue me.

Miley Cyrus: “If I Could Turn Back Time”

2024’s Cher is 1989’s Miley Cyrus. Or something like that. Say what you want about Billy Ray’s daughter, but she had the second-best performance of this year’s Grammy’s when she dripped herself in spite while performing “Flowers,” and you can’t convince me her rugged, soulful pop vocals wouldn’t do justice to one of Cher’s biggest hits. This almost makes too much sense.

Billie Eilish: “The End Of The Innocence”

Speaking of making too much sense, let’s Euro-fit this Don Henley classic, leave all of the room for all of the electronics to breathe in spaces never before heard, and let Billie explore each corner of the eerie atmosphere it would embody. Especially at this transitional point in her career (she only just turned 22 years old), this thing would be an entire mood.

Jelly Roll: “Love In An Elevator”

Hey. Why not? It’s not like Aerosmith will be hitting the road anytime soon.

Taylor Swift: “Blame It On The Rain”

All right, Taylor. Let’s see if that wry sense of humor you sometimes like to display is all it’s cracked up to be. The biggest frauds in the history of pop music meet the biggest popstar of the last 20 years. Talk about a Tortured Poets Department. This is either the best idea or worst idea here and there is no in between.

Olivia Rodrigo: “Wicked Game”

First, did you know this year is the 35th anniversary of Chris Isaak’s crowning achievement? Second, with all the angst, spite, anger and passion Rodrigo brings to the pop music landscape these days, I’d pay Real American Dollars to see how she’d interpret this gentle sultry classic. If anyone could find the vinegar in this song in 2024, The Immaculate Cusser ought to be the one.

Justin Timberlake: “Another Day In Paradise”

JT is on the comeback trail with “Selfish,” but it’s going to be awfully intriguing to see how the general public responds to him after the whole Britney Spears stuff from last year. Another perpetually intriguing pop star from years past? Phill Collins, who always felt like he was in on the joke as much as Timberlake likes to pretend he is. Imagine Timberlake calling Timbaland to spruce up the drum machine for this song and watch as the Mickey Mouse Club alumni attempts to pull on our heartstrings.

Doja Cat: “Head Like A Hole”

Utter chaos. That’s what this would be. Utter chaos. And precisely how Trent Reznor would want it.

Noah Kahan or SZA or Adele: “Yer So Bad”

OK, I’m cheating on this one, but hear me out. Tom Petty’s “Full Moon Fever” is an embarrassment of riches. “Free Fallin.” “I Won’t Back Down.” “Running Down A Dream.” But this little ditty has always been my favorite cut of them all. It’s so simple, it’s novel with its charm. Kahan could keep it semi-traditional. SZA could translate it into a murder story. And Adele could ballad-ify it with a wink and nod. Don’t tell me you wouldn’t be curious to hear all three … right?

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