Kenny Chesney Recalls Taking His Grandma on Her First Flight With Oprah in Heart Life Music
6 Video Views·Jan 24, 2026
Kenny Chesney Recalls Taking His Grandma on Her First Flight With Oprah in Heart Life Music
Oprah Winfrey had invited us to do the show, and she wanted me to do a first that I've
never done.
And they said, well, let's go throw out the first pitch at a Cubs game, because it's Chicago,
or she knew I love the Red Sox, and maybe the Red Sox, and I said, I've done both.
She thought about something else, and so I said, let me think about it a second.
And they said, what about if it's not me, but what if, you know, my grandmother at the
time was 88, I think, when we did this.
I said, what about us do something and capture something my grandmother has never done?
And she was, I think, 88, but late 80s, and had never been on an airplane in her life.
So I went to Knoxville and picked up my grandmother, my Aunt Sharon, and my mother, and I flew
her to Key West, Florida, just to have lunch at one of my favorite restaurants down there,
and to see her, as we were landing in Key West, look out the window and see, she had
never seen the ocean with all those different colors.
And I watched her, and it was as if she was, I mean, she was 88, but it was like she was
a child for the first time getting to see something that she had never seen.
And I was so happy and proud that we did that, you know, it meant the world to me.
That's my favorite memory with my grandmother, but in this book, you're going to be on that
ride with us, you know, and she loved iron skillet cornbread, and so she didn't believe
that anybody could make cornbread as good as hers, but she loved it, and she loved the
key lime pie, she loved everything, and it was one of those moments that I truly treasure
as a bonding moment with my grandmother later in her life.

