Bentley penned this song with Chris Tompkins and Josh Kear. It tells the story of a guy who is left standing alone at the alter but finds the strength to forge ahead on a solo trip to Cancun. Bentley recalled: "(I)went in to write with those guys, and had an idea. Josh threw that idea out, and he said, 'I always wanted to write a song called 'Drunk on a Plane.' Of course, I'm obsessed with planes, so I'm like, 'I love that! I've got to have a song called 'Drunk on a Plane.' Just thinking about the idea of being drunk on a plane and all the crazy things that could happen or do happen."
"It was really fun writing with those guys, just kind of creating this idea of this story of this guy who had been left at the altar, and just the ups and downs and the highs and lows of being on a plane and being drunk," Bentley continued. "I knew when I wrote it, it would go over great live. Like I could just take my guitar and go and play it in front of an audience that had never heard it before and get a laugh and entertain with that song, but I didn't know if it'd make the record or not."
Bentley is a licensed pilot, and when he sang the song at the 2013 Country Radio Seminar in Nashville, the host asked him if he was advocating flying an aircraft while intoxicated. "No, it's more of a Southwest situation," he assured the audience.
The Riser album was written and recorded in the year following the death of Bentley's father. The songs chosen for the record tell the of the ups and downs the singer went through, ranging from the loss of his dad to the birth of his third child, Knox. Bentley said at a private listening party on Nashville's Music Row that some of the tracks "don't really fit in the Riser theme, but there's a similar sound that makes it work together."
He added: "A song like 'Pretty Girls' or 'Drunk On A Plane' can fit as a pressure relief valve to get away from it, then bring it back. I wanted the album to be heavier and a little darker. I think a good country album should have a little bit of it all."
Bentley told the story of the song to Jam! Music: "I actually fly a small single engine, I fly it back and forth to some concerts, it helps me get me some more family time which is nice ... it's fun if you're up for that kind of thing," he said. "So anything about planes I love. So it became this title Drunk on a Plane. Just being natural songwriters and making up this story about this guy. 'Why is he drunk on a plane? Well, he got stood up at a wedding. Oh my gosh.' It's just a really fun song."
Bentley performed the song with Sheryl Crow at the 2014 ACM Awards. Crow first heard the song soon after it was written, and she immediately loved it.
The song's music video was directed by Wes Edwards and conceived by Bentley, Will Ferrell and Adam McKay of the website Funny or Die. The clip, which was shot in at Air Hollywood in a warehouse full of old planes in April 2014, stars Dierks as Captain Bentley for Riser Air. The country star also plays one of the regular passengers, which also include various band members and friends recruited by Bentley including comedian Jeff Dye and actress Emma Fitzpatrick (The Collection).
The visual was one Bentley had been thinking about for a long time. "Since the day I wrote this song I've been thinking about this video," he said. "Everyone that's heard this song has been thinking about the video for it."
The idea for the music video was inspired by an old joke between Edwards and his friends. The director remembered in a Songfacts interview
: "My friends and I used to joke around, and we used to make up bad country songs and sit around and sing them. We would try and come up with the most ridiculous scenarios possible and there was this joke song that we made up called 'Let's Land This Thing,' and it was exactly the plot of 'Drunk on a Plane.' A guy gets on a plane, he's too shy to talk to the girl, but then the plane starts going down and in the song he actually marries her on the way down. We were going to do that with "Drunk on a Plane," that's why we had the priest sitting there. He was going to perform the ceremony, but we ran out of time and it felt too complicated, so we went with let's just do it where he puts the ring on her finger and now they're engaged. I think that works just as well, but that actually came from this silly joke song that me and my friends made up probably 10 years ago. You never know where the idea is gonna come from."
The music clip won the Video of the Year trophy at the 2015 ACM Awards.