The Boot Staff
20 Years Ago: Dierks Bentley Earns First No. 1 Hit With ‘What Was I Thinkin”
On Sept. 27, 2003, Bentley earned his first No. 1 hit with "What Was I Thinkin'," from his self-titled freshman album.
21 Years Ago: Tim McGraw Hits No. 1 With ‘Something Like That’
On Sept. 25, 1999, McGraw earned his 10th No. 1 hit with "Something Like That."
27 Years Ago: Trisha Yearwood Hits No. 1 With ‘XXX’s and OOO’s (An American Girl)’
On Sept. 10, 1994, Yearwood's single "XXX's and OOO's (An American Girl)" became her second No. 1 hit.
33 Years Ago: Keith Whitley Hits No. 1 With ‘I Wonder Do You Think of Me’
Sept. 9, 1989, was a bittersweet day for friends and family of the late Whitley.
44 Years Ago: Willie Nelson and Leon Russell Share No. 1 Spot With ‘Heartbreak Hotel’ Remake
On Sept. 1, 1979, Nelson and Russell hit the No. 1 spot with their remake of the Elvis Presley hit "Heartbreak Hotel."
42 Years Ago: Charlie Daniels Earns Gold Single for ‘The Devil Went Down to Georgia’
On Aug. 21, 1979, Daniels earned a gold single for "The Devil Went Down to Georgia," from his 'Million Mile Reflections' album.
Top 25 Luke Bryan Songs
Which one is your favorite?
32 Years Ago: Dolly Parton Reaches No. 1 With ‘Why’d You Come in Here Lookin’ Like That’
On Aug. 5, 1989, Parton soared to the top of the charts with her single "Why'd You Come in Here Lookin' Like That."
33 Years Ago: Reba McEntire Hits No. 1 With ‘Cathy’s Clown’
On July 29, 1989, McEntire earned her 13th No. 1 single with "Cathy's Clown," which was originally recorded by the Everly Brothers.
32 Years Ago: George Strait Hits No. 1 With ‘What’s Going on in Your World’
On July 22, 1989, Strait soared to the top of the charts with his single "What's Going on in Your World."
Top 10 Chris Stapleton Songs
What would you add?
30 Years Ago: Garth Brooks’ ‘That Summer’ Hits No. 1
On July 3, 1993, Brooks earned his 10th No. 1 hit with "That Summer."