10 Unforgettable Country Songs Turning 25 In 2025

Unforgettable hits by George Strait, Jo Dee Messina, Rascal Flatts, LeAnn Rimes and many other artists are turning 25 years old in 2025.

Country’s biggest staples during the year 2000 included Lee Ann Womack’s “I Hope You Dance,” “Prayin’ For Daylight” by Rascal Flatts (a trio marking their 25th anniversary with a reunion tour this year), “It’s a Great Day to Be Alive” by Travis Tritt, and much more. Many of the genre’s fans also continued listening to iconic late 90s singles by Faith Hill, Tim McGraw, Toby Keith, Lonestar, The Chicks, Reba McEntire and others. Many of these artists blazed trails and serve as inspirations to today's powerhouse singer-songwriters and rising stars in the genre.

Artists released tons of beloved country songs in the year 2000. Here’s a list of just 10 of them that are turning 25 in 2025:

Lee Ann Womack, “I Hope You Dance”

Jo Dee Messina, “That’s The Way”

George Strait, “The Best Day”

Sara Evans, “Born To Fly”

LeAnn Rimes, “I Need You”

Rascal Flatts, “Prayin’ For Daylight”

Travis Tritt, “It’s a Great Day to Be Alive”

Kenny Chesney, “Don’t Happen Twice”

Alan Jackson, “Where I Come From”

Phil Vassar, “Just Another Day In Paradise”