Could I add “The Weight” (Robertson)?
Actually, a ton of The Band stuff…
“Virgil Caine is the name and I served on the Denver train…”
Hello Darling (Conway Twitty)
Poncho and Lefty (As performed by Haggard and Nelson)
Luckenbach, Texas (Waylon Jennings)
Georgia on My Mind (as performed by Willy Nelson)
Witchita Lineman (Glen Campbell)
Walkin’ After Midnight (as performed by Cline or Garth Brooks)
Passenger Side (Wilco)
Tennessee Waltz (as performed by Patsy Cline)
I’m So Lonesome I Could Cry (Williams Sr)
A Country Boy Can Survive (Williams Jr)
OK, OK, but is The Band country or not? 
Whiskey Lullaby–Brad Paisley and Allison Krauss
He’ll Have To Go–Jim Reeves
Heaven In My Woman’s Eyes–Tracy Byrd
Shake the Sugar Tree–Pam Tillis
How Can I Help You To Say Goodbye–Patty Loveless
Beautiful Goodbye–Jennifer Hanson
Bring On the Rain–Jo Dee Messina (featuring Tim McGraw)
When I Said I Do–Clint and Lisa Hartman Black
It’s Just A Matter Of Time–Randy Travis
Carryin’ Your Love With Me–George Strait
Not necessarily in order, and with only one song per artist:
- “He Stopped Loving Her Today,” George Jones
- “I’m So Lonesome I Could Cry,” Hank Williams Sr.
- “I Walk the Line,” Johnny Cash
- “She’s Got You,” Patsy Cline
- “In the Good Old Days (When Times Were Bad),” Dolly Parton
- “All My Friends Are Gonna Be Strangers,” Merle Haggard
- “Wings Upon Your Horns,” Loretta Lynn
- “Long White Cadillac,” Dwight Yoakam
- “Don’t Put No Headstone on My Grave,” Jerry Lee Lewis [and an honorable mention for Charlie Rich’s original]
- “You Never Even Called Me By My Name,” David Allen Coe
Kenny Chesney - “There Goes My Life”
Randy Travis - “Three Wooden Crosses”
Braid Paisley and Allison Krausse - “Whiskey Lullabye”
Martina McBride - “Concrete Angel”
John Michael Montgomery - “Little Girl”
Johnny Cash - “Ring of Fire”
Patsy Cline - “I Fall To Pieces”
George Jones - “He Stopped Loving Her Today”
Tanya Tucker - “Two Sparrows in a Hurricane”
Lee Ann Womack - “I Hope You Dance”
Could easily do twenty…
Riley Puckett, “Ragged But Right”
Carter Family, “I Ain’t Gonna Work Tomorrow”
Milton Brown, “Taking Off”
Bob Wills, “Stay All Night (Stay a Little Longer)”
Delmore Brothers, “Blues Stay Away From Me”
Hank Williams, “(I Heard That) Lonesome Whistle”
Al Dexter, “WIne, Women and Song”
Johnny Cash, “Folsom Prison Blues”
Lefty Frizzell, “The Long Black Veil”
Bobby Bare, “Detroit City”
Dolly Parton, “Jolene”
George Jones, “The Grand Tour”
Buck Owens, “Close Up the Honky Tonks”
Johnny Darrell, “Why You Been Gone So Long”
John Anderson, “Wild and Blue”
In no order:
You Never Even Call Me By My Name–David Allan Coe
Folsum Prison Blues–Johnny Cash
Gentle on My Mind–Glen Campbell
I Fall to Pieces–Patsy Cline
Flowers on the Wall–Statler Brothers
Guitars, Cadillacs–Dwight Yoakam
Much Too Young–Garth Brooks
Someday Soon–Suzy Boggus
Mama Tried–Merle Haggard
Wurlitzer Prize–Waylon Jennings and Willie Nelson