10 ’90s Kenny Chesney Songs We’re Still Playing on Repeat

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Kenny Chesney has become one of the biggest country stars of our generation. He did it the old fashioned way, too: he worked his butt off.

While he’s duetting with P!nk and winning awards with “American Kids,” let’s not forget where he came from (and I don’t mean Luttrell, Tenn.).

Kenny was a ’90s country singer, who — from 1993 to 1999 earned eight Top 10 hits and three No. 1s — gave us some of our most beloved songs of the decade.

Here’s a look back at Kenny’s early career and the hits that built the foundation for his superstardom:

1. “Fall in Love”

The way Kenny sings “bouquet” is my favorite thing.

2. “Grandpa Told Me So”

This song is a little tough to listen to since I no longer have any grandparents, but it reminds me so much of my grandpa that every now and then I risk the tears and give it a listen.

3. “Me And You”

This is (and always will be) one of my favorite love songs. Timeless

4. “Back Where I Come From”

This has been a concert favorite of Kenny’s and I don’t blame him.

5. “She’s Got It All”

This is just fun and indicative of early Kenny.

6. “That’s Why I’m Here”

If you’re in the mood to be more serious for a moment, this song may break your heart but it will do it so well.

7. “What I Need to Do”

This song is also on the sad side, but it’s so good.

8. “How Forever Feels”

I can’t help but going back to high school when I hear this song. This was Kenny’s first big hit that I remembered and I listened to it on repeat. Also, it was his first beach video.

9. “You Had Me From Hello”

OK, this may be a little awkward to listen to — since Kenny divorced the person who said the line’s inspiration in Jerry MaGuire … ahem Renee Zellweger — but it’s still pretty fun.

10. “She Thinks My Tractor’s Sexy”

Arguably, the biggest early hit of Kenny’s career is a classic. Have a little fun and out it on.

90s Kenny Chesney Songs