Songfacts®:

• This bluesy country ballad finds a jilted Carrie Underwood sitting alone in a bar nursing a whisky. She notices a dude across the room who also seems down on his luck. Underwood invites him to join her and they end up sharing the evening together.
  
  Underwood makes it clear to the guy she's not picking him up – she considers him to be just a drinking buddy who is feeling just as low as she is.
• The picture of Carrie Underwood pouring whiskey to numb heartache is at odds with her good-girl persona. In fact, "Drinking Alone" was the second successive single dropped by the singer that challenged the assumptions of her squeaky-clean image. Her previous release was "Southbound," a party song that also contains a number of alcohol references.
• Underwood wrote the song with her producer, David Garcia, and songwriter Brett James. The same trio also penned Cry Pretty's second single, "Love Wins."
• Carrie Underwood gave the debut televised performance of the song at the 2019 CMAs on November 13, 2019. Donning a fedora, she performed a jazzy version of the tune on a stage setting suggesting a speakeasy.
• Carrie Underwood said she's happy "Drinking Alone" didn't end up as a typical rebound relationship song.
  
  "I feel like the title could have gone to a very like sad emotional place, but me being me, I still wanted to have that strong kind of character in there. So, I love the fact that this is a breakup song," she explained. "'I'm here at the bar drinking my pain away. You and me can hang out. Why should we both be lamenting over lost love separately? We're both here doing the same thing. Let's just do that together.'
  
  I love that the character, I was like I don't want her like going home with him. I don't want any of that. I just want it to be like, 'Okay we'll just hang out. We'll drink. We'll maybe share a corner booth kiss.'"
• Filmed in muted colors, the Randee St. Nicholas-directed video features Underwood in dual roles. We see her depicting both a seductive lounge singer crooning the song in a dimly-lit club, and a woman who is drawn to a visibly dejected guy. The two, each nursing heartbreaks, cuddle in their booth, but they don't go home together.
  
  Randee St. Nicholas has worked with Underwood on several previous occasions, including shooting her CMT Award-winning "Blown Away" clip.
• Carrie Underwood walked away with both the Video of the Year and Female Video of the Year prizes for this song at the 2020 CMT Awards. Her 21st and 22nd CMT trophies, they added to Underwood's record as the most successful artist in the show's history.