Dolly Parton
As a country music artist, songwriter, and actress, this was her most successful movie.
What is 9 to 5?
This person is considered the most successful country artist of the 90s.
Bonus: First number 1 song
Who is Garth Brooks?
If Tomorrow Never Comes
This famous pop star released her first single on the country charts in 2006.
Hint: "Tim Mcgraw"
Who is Taylor Swift?
Hank Williams Jr's high energy anthem "All My Rowdy Friends Are Coming Ober Tonight" was adapted to open the broadcast for which major sports television staple?
Bonus: She sang the anthem for Sunday Night Football.
What is Monday Night Football?
Who is Carrie Underwood?
Morgan Wallen spent a record-shattering 16 weeks atop the Billboard Hot 100 with this 2023 hit.
What is "Last Night"?
Dolly had this many siblings.
What is 11?
the most successful female 90s country artist.
Bonus: First number 1 hit.
Where is she from?
Who is Shania Twain?
Any Man of Mine
Canada
This collaboration between Blake Shelton and Post Malone won Music Video of the Year in 2024.
What is Pour Me a Drink?
In George Strait's iconic 1981 hit "Amarillo By Morning" the narrator is traveling to Texas to compete in this specific grueling sport.
What is bull riding?
This country star completed 1 year of college in engineering at Vanderbilt U.
Who is Chris Stapleton?
She re- recorded this number 1 hit of Dolly Parton's and it also rocketed to #1 on the pop charts.
Bonus: Name of the Dolly Parton movie and the Whitney Houston movie...
Who did each actress play opposite
Who is Whitney Houston?, I Will Always Love You
The Best Little Whorehouse in Texas, The Bodyguard
A successful performer in her own right, she is married to Garth Brooks.
Bonus: Her first number 1 hit in 1991. The first #1 debut single by a female country artist since 1964.
(Connie Smith)
Who is Trisha Yearwood?
What is She's In Love With the Boy
This unlikely duo's collaboration spent 8 non-consecutive weeks at #1 on the country charts in 2003; the most successful single of this 90s country artist's career.
What is It's Five O'clock Somewhere?
By Alan Jackson and Jimmy Buffet
This multi ACM and CMA award winning artist is well- known for a deep love of horses, owning a huge horse farm and actively incorporating equestrian elements into her lifestyle.
Hint: She has a clothing line at Boot Barn
She was once married to Blake Shelton.
Who is Miranda Lambert?
Luke Combs emotional and massively successful 2023 cover of this artist's classic 1988 song won single of the year at the CMA Awards and remains a career-defining crossover hit.
Who is Tracy Chapman? "Fast Car"
Dolly performed the most duets with this man.
(1974)
She had her most commercial success with this man.
Who is Porter Wagoner?
Kenny Rogers. Islands in the stream. Written by the Bee Gees
The most played country radio song of the 90s.
What is Should've been a cowboy?
Toby Keith, 1993. He also wrote it.
Chris Stapleton co-wrote the poignant, nostalgic track "When we were young" alongside this international pop icon.
Who is Adele
Vince Gill is celebrated for his vocal range and mastery of multiple instruments, and is also an elite scratch-level athlete in this sport.
What is the most boring game ever invented?
This daughter of billionaire Groupon founder and current CEO of Tempus AI, Eric Lefkofsky, had her 2026 single, "Boston" peak at #2 on the US Billboard Hot 100.
Who is Stella Lefty?
Dolly's famous god-daughter.
Also, after genealogy testing, discovered they are 7th cousins.
Who is Miley Cyrus?
In 2017, this famous country singer was inducted into the country music Hall of Fame by Loretta Lynn.
Bonus: He had 35 #1 hits, of which he wrote or co-wrote 26.
Who is Alan Jackson?
This famous rapper recorded an entire album with collaborations with country artists, like Luke Combs, Bailey Zimmmerman, Darius Rucker, and Ella Langley.
Who is BigXthaPlug?
This dedicated baseball fan and country music star has frequently participated in pre- game drills, batting practice, and signed an honorary 1 day contract with the Boston Red Sox.
Who is Kenny Chesney?
The unofficially most played song on country radio from Oct 1 to Oct 4, that can render 2 people on a road trip across the US want to stick an icepick in our ear.
What is "Boston" by Stella Lefty?