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Watch Chris Stapleton and Jimmy Fallon Perform 'You Should Probably Leave'

Chris Stapelton returned to one of our favorite late-night shows, "The Tonight Show Starring Jimmy Fallon" where he performed "You Should Probably Leave" with a special guest. Who was that guest? None other than the host himself! Fallon sang some harmony vocals, played rhythm guitar, and even had a small one-note solo.

Before his performance, Fallon stated, "It's an interesting kind of performance tonight because we have the great Chris Stapleton here to do his hit song 'You Should Probably Leave,' off of his new album Starting Over. I got a text last night from Chris saying that his guitarist, Dave Cobb, has an earache and so he could not travel, he could not fly on a plane. ... He said, 'so I need a guitarist' and I said to Chris, 'say no more.'"

Stapleton is having a great year so far as a leading nominee at the 55th Annual CMA Awards with nominations in five different categories. The country singer is nominated for Male Vocalist of the Year, Album of the Year, Entertainer of the Year, Song of The Year and Single of The Year.

The country music star is currently on his extensive All-American Road Show Tour with stops included in Nashville's Bridgestone Arena, New York's Madison Square Garden, and Washington State's Gorge Amphitheater. The singer is also scheduled to perform at the University of Kentucky Kroger field on April 23, 2022, which will be the first-ever held at Kroger field. The concert will feature special guests Willie Nelson and Family, Yola and Sheryl Crow.

The proceeds will benefit Stapleton's Outlaw State of Kind Hometown Fund. The fund was established in partnership with the Bluegrass Community Foundation and specifically supported national and local organizations that directly impacted Kentucky with initial grant distribution focusing on music and arts education.

Chris Stapleton's "All-American Road Show"

  • October 7—Syracuse, NY—St. Joseph's Health Amphitheater at Lakeview^
  • October 8—New York, NY—Madison Square Garden+
  • October 9—Holmdel, NJ—PNC Bank Arts Center^
  • October 14—Columbia, MO—Mizzou Arena+
  • October 15—Lincoln, NE—Pinnacle Bank Arena+
  • October 16—Sioux Falls, SD—Denny Sanford PREMIER Center+ (SOLD OUT)
  • October 21—Cincinnati, OH—Riverbend Music Center+
  • October 22—Nashville, TN—Bridgestone Arena+ (SOLD OUT)
  • October 23—Nashville, TN—Bridgestone Arena+ (SOLD OUT)
  • October 28—Lubbock, TX—United Supermarket Arena**
  • October 29—Albuquerque, NM—Isleta Amphitheater**
  • October 30—Phoenix, AZ—Ak-Chin Pavilion** (SOLD OUT)
  • November 4—Austin, TX—Frank Erwin Center** (SOLD OUT)
  • November 5—Tulsa, OK—BOK Center** (SOLD OUT)
  • November 6—The Woodlands, TX—Cynthia Woods Mitchell Pavilion** (SOLD OUT)
  • November 13—Minneapolis, MN—U.S. Bank Stadium%%
  • November 18—Orlando, FL—Amway Center^
  • November 19—Estero, FL—Hertz Arena^ (SOLD OUT)
  • November 20—West Palm Beach, FL—iTHINK Financial Amphitheatre^
  • December 3—Memphis, TN—FedEx Forum+
  • December 4—Biloxi, MS—Mississippi Coast Coliseum+ (SOLD OUT)
  • December 5—Knoxville, TN—Thompson-Boling Arena+
  • April 20, 2022—Toledo, OH—Huntington Center^^
  • April 21, 2022—Columbus, OH—Schottenstein Center^^
  • April 23, 2022—Lexington, KY—A Concert for Kentucky - Kroger Field##
  • June 2, 2022—Nampa, ID—Ford Idaho Center Arena??
  • June 3, 2022—Ridgefield, WA—Sunlight Supple Amphitheater?? (SOLD OUT)
  • June 4, 2022—George, WA—Gorge Amphitheater?? (SOLD OUT)
  • June 11, 2022—San Bernardino, CA—Glen Helen Amphitheater??
  • June 16, 2022—Bakersfield, CA—Mechanics Bank Arena??
  • June 17, 2022—Wheatland, CA—Toyota Amphitheatre??
  • June 18, 2022—Mountain View, CA—Shoreline Amphitheatre??
  • June 23, 2022—West Valley City, UT—Usana Amphitheater§§
  • June 24, 2022—Denver, CO—Ball Arena§§
  • June 25, 2022—Denver, CO—Ball Arena§§

Editors Note: This article was originally published on October 6, 2021.