Songfacts®:

• Nick Lowe told The A.V. Club that this song is a lighthearted look at death: "It's funny how that song seems to interest people, judging so far from the people I've spoken to. I try to avoid writing autobiographical songs. I write about what I know, but I'm one of those people, like Randy Newman, who make up a character and then make them say stuff. It's not really me; it's just a character I've made up. But this thing does actually say, 'I'm 61, and I thought I'd never make 30.' And the reason for that is, I was sitting at home watching the television and fiddling around with the guitar, and I came up with a tune. And I'd just heard Johnny Cash singing, 'I'm 61 years old, I never thought I'd see 30.' I can't remember if those were the actual words, but that was the idea. I just heard Johnny Cash sing that, and it just went from there. I can't honestly say whether it's morbid, in that, 'Here I am, considering the Grim Reaper tapping me on the shoulder. It's time for me to get my thoughts out.' It's much more joking for me, really."
• Lowe confessed to Terry Gross of Fresh Air that he did not think he would make it past 30, as the lyrics state: "I might be in any kind of walk of life, but when you were young, and especially if you were in, as I was, in rock 'n' roll bands in the 1970s, when everybody seemed to be very excited about everything, it was - there were quite a lot of opportunities for disaster to befall a lusty young man. You know, climbing out of windows and along the - I mean, I remember climbing out of a hotel window, you know, to surprise someone who was in the room next door, you know, sort of five or six stories up."
• The Old Magic was Lowe's thirteenth solo album. Lowe told The Huffington Post that "Checkout Time" was one of the first songs that he wrote for the record.