The JOAT 50 Song Countdown is a blog series where every weekday for 10 weeks I am posting a brand new long form essay where I have ranked and written about my 50 favorite songs of all-time. From Adele to Zac Brown Band, Patsy Cline to Plasma Canvas, Ludacris to Rise Against, this series offers a personal essay about the 50 songs that hit me the absolute hardest.

Bear with me here through a bit of a detour to start. When I was in middle school I was obsessed with the Christian Slater film Kuffs, which I wrote about here. I saw this character as aspirational because, as I summarily put it in that piece, “Kuffs mouths off to authority figures, gets quippy with bad guys who have guns in his face, and dances shirtless with Milla Jovovich in her underwear at the movie’s beginning.” Like most of the PG-13 movies from that era, it’s surprisingly violent, all over the place tone-wise, and totally preoccupied with its romantic subplot.

Kuffs has knocked up his girlfriend who’s like 18 years old (Kuffs himself is only 21), so like a dick, he leaves her, but later regrets it and tortures himself over what to do about it, what to do about her, and how to grow up after his cop brother has been gunned down by hoods. In one scene he sits on the corner of the bed, calls her, but doesn’t know what to say while she sits on the other end knowing it’s him and tries to cajole him into speaking. Kuffs buries his face in his free hand and hangs up silently.

Soundtracking this scene is a song called “I Don’t Want To Live Without You” by Gregg Tripp. It’s a power ballad that you can smell the stink of 1992 sensibility on from miles away. Some hints of hair metal with no hint of the coming grunge revolution. This song goes to the same family reunion attended by Mr. Big’s “To Be With You” and Extreme’s “More Than Words.” And what do all three of these songs have in common? They all fucking suck.

I swear I’m getting to Macy Gray. Hang in there.

The emotions are all overwrought, the lyrical sentiment is extremely on-the-nose, and every single one of these guys feels like they’re cosplaying as some Sensitive Dude who really just wants you to fawn over him and his guitar so he can get a handjob. In other words, perfect sensibility for 13 and 14 year-old me!

And sure, while I was as horny as any boy that age, at heart I was a romantic. Or at least I wanted to be. I used to FALL HARD for girls I was crushing on, but I’d be too chickenshit to call them and tell them that. I wanted that feeling in return from someone, and for a long time the closest I got was watching that scene in Kuffs over and over again because that’s how I thought it looked and felt. The Gregg Tripp song under it became my stupid “romantic guy” anthem.

The song “I Try” by Macy Gray actually captures the feeling I was trying to manufacture watching Kuffs all those times. That nervous excitement. That shaky optimism. That delightful mental preoccupation. That flush of so many emotions that cause you to choke, stumble, and be otherwise klutzy when you’re trying to look cool. You think – hope! – the object of your affection is feeling the same way, but you never know for sure and that tension, while not exactly enjoyable, is extremely animating.

Macy Gray’s soft, sweet, unusual, off-kilter delivery gives the song its unique stickiness. I’d be willing to bet even if you haven’t heard or thought about this song in years, you could recall it with stunning clarity. And I know this because one time while visiting Kristin’s sister and her family out of state, they invited some of their friends over and I told one of them about how great it is to take a few hits off the pen, listen to this, and sing along with friends. She couldn’t even remember the song based on my description, but once that pen got passed, I queued it up, and like magic, everyone, all 10 of us, were singing along with Macy’s weird, raspy delivery remembering what 1999 felt like. The doubter took a huge rip and then pointed at me and said with her heart, “You were so right, bro! This shit is incredible.”

It’s hard to imagine anyone trying to do a cover of this simply because Gray’s voice is so distinctive and her delivery so anachronistic. It’s like why it’s a terrible idea to try and imitate Willie Nelson or Brian Johnson from AC/DC during karaoke.  Maybe this also explains why I can’t name a single other Macy Gray song, and I’ll bet you can’t either. I think it’s possible we all heard this one, and then our brains collectively decided it was the only song they wanted to associate her with forever. It’s indelible, which is to Macy Gray’s credit, but also probably to her chagrin. Although she seemed to do okay for herself in both music and acting, if her Wikipedia page is accurate. I have no reason to believe it isn’t.

When I hear this song, it feels like I’m floating. It’s a vibe unto itself. And even though I’ve been with Kristin exclusively for nearly 20 years now, this song is like putting on a magic coat where you get to sit in those wonderful, nerve-wracking feelings of romantic possibility and opportunity. And I don’t think I’m alone because one night I posted this on Facebook five years ago:

Public service announcement: Kristin and I have reached the point in the evening where we are singing along to Macy Gray together interspersed with fits of laughter. Fair warning to anyone who attempts to contact us.

I don’t care who you are or what your sensibility is, get high with the person you love and listen to this song. You won’t regret it.

Up next: I just want to ask, hey whatcha doin?