Country music is storytelling and familiar voices, but do you recognize the faces behind the twang? We’ve rounded up 100 of the genre’s greatest artists. See how many you can identify from a single photograph.
Each question gives you four plausible singers, and the wrong answers aren’t easy to dismiss. You’ll meet pioneers, outlaws, and modern superstars—with answers shuffled so patterns won’t save you.
Whether you were raised on classics or just found country, this quiz will remind you how varied the scene is. Grab your friends and see who really knows their legends.
[D] George Strait | The "King of Country" who sold over 100 million records and refuses to wear anything but a cowboy hat on stage.
2/30
2. Johnny Cash
[A] Johnny Cash | The Man in Black walked the line between outlaw and gospel, recording in Folsom Prison and creating timeless American mythology.
3/30
3. Alan Jackson
[A] Alan Jackson | Remember when he wrote "Where Were You" after 9/11? This Georgia native turned small-town stories into 35 number-one hits.
4/30
4. Hank Williams
[A] Hank Williams | Dead at 29, yet his 35 singles in 5 years built country music's foundation—proof that some flames burn brightest when brief.
5/30
5. Waylon Jennings
[B] Waylon Jennings | Gave up his seat on Buddy Holly's fatal flight, then spent decades as the leather-vested rebel who helped invent outlaw country.
6/30
6. Merle Haggard
[D] Merle Haggard | From San Quentin inmate #A45200 to presidential pardon recipient, "Mama Tried" wasn't just a song title.
7/30
7. George Jones
[D] George Jones | Once drove his lawnmower to a liquor store when his wife hid the car keys—the "Possum" lived country music as hard as he sang it.
8/30
8. Willie Nelson
[B] Willie Nelson | The IRS tried to take him down in '90, but you can't kill a legend who's smoked pot on the White House roof.
9/30
9. Dolly Parton
[A] Dolly Parton | "It costs a lot of money to look this cheap," says the woman who turned "9 to 5" into an empire and gave away 200 million books.
10/30
10. Brooks & Dunn
[D] Brooks & Dunn | Twenty years, 20 number-ones, and "Boot Scootin' Boogie" made line dancing mandatory at every wedding in the '90s.
11/30
11. Randy Travis
[C] Randy Travis | His 1986 "Storms of Life" saved country music from synth-pop invasion, bringing back the steel guitar when Nashville needed it most.
12/30
12. Reba McEntire
[B] Reba McEntire | Survived a plane crash that killed eight band members in '91, then conquered Broadway, sitcoms, and sold 75 million albums.
13/30
13. Loretta Lynn
[D] Loretta Lynn | The Coal Miner's Daughter who sang about birth control pills in 1975 when radio wouldn't even say the word "pregnant."
14/30
14. Toby Keith
[B] Toby Keith | Former oil field worker who turned "Red Solo Cup" into America's unofficial party anthem and built a restaurant empire.
15/30
15. Conway Twitty
[C] Conway Twitty | Hold the record with 40 number-one country hits—started as a rockabilly Harold Jenkins before that name change magic.
16/30
16. Patsy Cline
[C] Patsy Cline | Died at 30 in a plane crash, but "Crazy" still breaks hearts 60 years later—Willie Nelson wrote it, she owned it forever.
17/30
17. Alabama
[C] Alabama | First country band to go platinum, these Fort Payne boys proved you could bring Southern rock to the Grand Ole Opry.
18/30
18. Kenny Rogers
[B] Kenny Rogers | The Gambler who knew when to fold 'em—except when it came to plastic surgery and rotisserie chicken franchises.
19/30
19. Hank Williams, Jr.
[C] Hank Williams, Jr. | Fell off a mountain in Montana, rebuilt his face, then asked if we were ready for some football every Monday night.
20/30
20. Garth Brooks
[B] Garth Brooks | The man who brought pyrotechnics to country concerts and outsold everyone except The Beatles—yes, even Elvis.
21/30
21. Chris Stapleton
[C] Chris Stapleton | Wrote hits for everyone else for a decade, then showed up at the 2015 CMAs with Justin Timberlake and changed country music overnight.
22/30
22. Travis Tritt
[B] Travis Tritt | The mullet-sporting "T-R-O-U-B-L-E" maker who brought Southern rock swagger back to '90s country radio.
23/30
23. Charley Pride
[D] Charley Pride | First Black superstar in country music who conquered prejudice with pure talent—29 number-ones don't lie.
24/30
24. Tim McGraw
[A] Tim McGraw | Discovered his father was baseball pitcher Tug McGraw at 11, then pitched perfect country hits while marrying Faith Hill.
25/30
25. The Charlie Daniels Band
[A] The Charlie Daniels Band | "The Devil Went Down to Georgia" featured the fastest fiddle solo in country history—Satan didn't stand a chance.
26/30
26. Don Williams
[B] Don Williams | The "Gentle Giant" whose whisper-soft baritone proved you don't need to yell to fill an arena.
27/30
27. Marty Robbins
[D] Marty Robbins | NASCAR driver, gunfighter ballad master, and the voice behind "El Paso"—the longest song to ever hit number one in country.
28/30
28. Dwight Yoakam
[A] Dwight Yoakam | Those impossibly tight jeans and Bakersfield sound rescued country from the Urban Cowboy era—plus he dated Sharon Stone.
29/30
29. Vince Gill
[C] Vince Gill | With 22 Grammys and a voice like Tennessee honey, he's the nice guy who finished first in Nashville.
30/30
30. Tammy Wynette
[A] Tammy Wynette | Five marriages, one to George Jones, and "Stand By Your Man" became feminism's most controversial country anthem.