This song is about Edwin McCain's struggle with alcoholism. It also touches on the superficiality of the music industry. In our interview with McCain, he revealed precisely how the song came about: "I went to New York and met up with Jason Flom, who was the president of Atlantic and the president of Virgin and is a huge figure in the music industry. He was the guy that signed me to my first deal, and a friend to me to this day...I was with him in New York and got invited to this industry thing by Tom Poleman from Z-100, he's a programmer for Clear Channel. He and I are good friends to this day, too. I'd been doing a lot of work, like playing for AIDS patients in the hospital and doing sort of karmic payback. He invited me to this banquet, and I found myself seated at a table with John Mayer and Jessica Simpson and Nick and Rob Thomas and all the label industry people and their new stars. And it was just that same old scene. I don't know, the lyric popped into my head, 'these organ grinders with their monkeys, and here we are.'" After the banquet, McCain stayed at New York's The Gramercy Hotel, which helped to influence the direction of the song: "The Gramercy was the cheapest place to stay. I mean, it was low-low rent. And I had to buy a shirt to be able to go to this event, because I didn't have anything good enough to wear. And I Just found myself laughing at that. I had been listening to a bunch of Randy Newman, so I had a healthy sarcastic feeling going, and man, that song - the welcome page on the Gramercy on the hotel TV was, 'Hey, welcome to the Gramercy.' They didn't have any amenities to brag about, they were just like, 'Babe Ruth used to get really drunk in our bar.' (Laughing) It was like a catalog of all these famous alcoholics, and at the time I was struggling with my own alcoholism, and I found it funny. I was thinking, Wow, what a coincidence. Me and Babe Ruth have been alcoholics in the same room. And here I am. So I was being sarcastic about my own struggles and everything else."

"Gramercy Park Hotel" contains the line: "And all the publicists sing 'La di da di da da'." McCain revealed his own publicist took offense to this mocking lyric: "At the time, I had this publicist that took umbrage with that. She was just irritated that I would say that."