Though his 2020-released and Country Music Association Album of the Year award-winning fourth studio album was entitled Starting Over, in many ways, the year represented a slightly better than usual year of business for 2021 CMT Artists of the Year honoree Chris Stapleton. In his two-decade career, he's penned as much critically acclaimed material for himself as he has for others. This has led to nine ASCAP Country Music Awards, five Grammy Awards, seven Academy of Country Music Awards, ten Country Music Association Awards, and three previous times being honored as one of CMT's Artists of the Year. However, 2021 found Stapleton emerging from the pandemic at a level wherein he may be at what can be best described as an elevated level of a creative peak.
The four singles released from Starting Over -- the album's title single, "Cold, "Arkansas," and "You Should Probably Leave" -- all achieved Top 40 Billboard charting status across the Hot 100, Rock, and Hot Country countdowns. Notably, "Starting Over" joined his 2015-released cover of David Allan Coe's "Tennessee Whiskey" as his second number-one hit, and his first written by him, for himself. When other Stapleton-written number ones include tracks like Josh Turner's "Your Man" and George Strait's "Love's Gonna Make It Alright," it highlights the level of greatness associated with his artistry. In considering the past twelve months as a place where the talent of Stapleton, the performer, was finally displayed in a manner that equaled the skill and legend of Stapleton, the writer, him receiving this honor feels particularly powerful.
At June 2021's CMT Music Awards, fans heard Stapleton's renowned tenor twice on the program. Foremost, he performed Starting Over track "Arkansas" from Bonnaroo Farms in Tennessee to help kick off the event. Later on, he joined Grammy and Academy Award-winning soul vocalist and guitarist HER for a rendition of HER's hit song "Hold On." Stapleton's growling blues and HER's silky, soaring style paired well. In a January 2021 iHeartRadio conversationwith fans, Stapleton first highlighted his appreciation of the rising superstar musician's talent, noting, "The artist I find most interesting right now is HER. She's an R & B artist and the real deal. She's just an awesome guitar player and singer. If something like that could take place, I would be into that a lot, just to see what would happen, because I'm so fascinated by her talent."
Moreover, on the CMT Music Awards red carpet, HER told CMT, "I always knew Chris and I would be a great musical fit. I've been a Chris Stapleton fan for the past five years. I saw him sing' Tennessee Whiskey' live, and that's what did it for me. As soon as I knew I was performing [at the 2021 CMT Music Awards], I knew that it would be great."
Stapleton was a live performance and collaborative favorite throughout quarantine's first wave. But, as our need to be socially distanced merged with our need to be entertained, songs on Starting Over that weren't even radio singles -- like the ballad "Maggie's Song" gained favor. Notably, Stapleton was joined by Miranda Lambert at Nashville's Bluebird Cafe during the 2021 ACM Awards for a performance of the album track regarding his love for his late pet dog. As well, Caylee Hammack's breakout hit "Small Town Hypocrite" was re-released in April 2021 with a feature from the "Broken Halos" singer to significant critical acclaim. Stapleton has also sung alongside Jimmy Fallon on his late-night talk program, on CBS Saturday Morning, plus joined Stephen Colbert, Jimmy Kimmel, and more.
Though he's won -- including his 2021 honor from CMT as one of the Artists of the Year -- an incredible multitude of honors, humility still grounds his superstar-level output. In a 2020 Vulture feature, the vocalist said, "I don't think about making music for awards or any other reason than trying to do something that I would like, or that I think is listenable or proper." Related, to GQ in November 2020, Stapleton added a point that more deeply highlighted his artistic motivations. The statement speaks, on a broader level as to how Stapleton exceeded his own high standard of excellence in the past year. "I lean into the music and hope that that's the thread that brings people on, and brings somebody some joy, and keeps that wheel keep turning. You can feel it when it's working, and you can feel it coming back at you on the stage, and that goes through your body, some magic, and then it comes back out to the audience, and you keep the give and take going."