WATCH: Jimmie Allen Tributes Toby Keith at the Grand Ole Opry With Performance Of ’90s Country Classic

Jimmie Allen honored Toby Keith with a rousing rendition of his 1993 debut single, “Should’ve Been a Cowboy” on the…


Lauren Jo Black

| Posted on

July 24, 2022

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Jimmie Allen; Photo via YouTube

Jimmie Allen honored Toby Keith with a rousing rendition of his 1993 debut single, “Should’ve Been a Cowboy” on the stage of the Grand Ole Opry. 

Alongside rising country duo Neon Union, Allen delivered a cover of the Toby Keith hit as fans in the Opry House sang and clapped along. 

Click below to watch the performance at the 1-hr mark.

The performance was filmed in partnership between Grand Ole Opry and Circle Network, as part of Opry Live: Opry Loves the ’90s, which aired on Circle Network in celebration of one of the most beloved decades in country music. 

The star-studded special also featured performances by Kelsea Ballerini, Cody Johnson, Midland, Michael Ray, Carrie Underwood, Keith Urban, Lainey Wilson and Chris Young.

The program showcased each of the artists covering popular ‘90s country hits from artists like Garth Brooks, Patty Loveless, The Chicks, Toby Keith, Vince Gill and more.

The one-hour concert also included an exclusive collaboration of the 1996 No. 1 hit “Strawberry Wine” between Deana Carter and Opry NextStage artist BRELAND. 

Hosted by Natalie Stovall, Opry Live: Opry Loves the ’90s premiered via Circle Network on Saturday, July 23 at 9/8c and re-aired at 12/11c. 

In May, the Grand Ole Opry launched a celebration of ‘90s country music with the limited-time “Opry Loves the ‘90s” experience. 

The exhibit showcases the artists, songs and songwriters that defined the decade with displays including iconic stage wear and artifacts representing career milestone moments. Performances from Opry members Clint Black, Garth Brooks, Terri Clark, Alan Jackson, Martina McBride, Reba McEntire, Lorrie Morgan, Marty Stuart, Travis Tritt, Trisha Yearwood and more are also featured throughout. 

Additionally, the Opry is commemorating the ‘90s with ‘90s-themed Opry Plaza Parties and surprise artist collaborations celebrating ’90s Country Music.

The Opry’s ’90s experience runs through the end of 2022 and continues across other Opry Entertainment Group properties including WSM Radio, Circle Network and, as well as across the Opry’s social channels. 
For more information and to purchase tickets, visit

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