Songfacts®:

• A style parody of Weezer, this tells the story of a once-promising actor who was forced to take a job as a Jungle Cruise tour guide at an amusement park when his budding career hit the skids. The song's wistful tone is not typical of Weird Al's work. The parody master told AV Club in 2011, "'Skipper Dan' is a bit more poignant than what I usually write. I still think it would qualify as a comedy song, but it's definitely a little more bittersweet. It's kind of a character study."
  
  He continued: "I was inspired one time when my family and I actually did go on the Jungle Cruise ride at Disneyland, and the skipper that we had just offhandedly referred to his failed acting career. Immediately, the bells went off in my head, and I thought, 'Well, here's a song right here.' So I created a whole backstory for this guy, and made him a very bitter failed actor who once had a promising career, and now his life has devolved into basically doing a seven-minute bad comedy routine 34 times a day."
• In the first verse, Dan recalls that his early days were full of promise. He graduated at the top of his class at Julliard, a private performing arts school in New York City, and studied his craft diligently to prepare for a Hollywood career. He says he "read my Uta Hagen and studied the Bard." Uta Hagen was a famed actress and drama teacher, while the Bard is a nickname for William Shakespeare.
• Dan's Hollywood fantasies have him hobnobbing with famous folks. In the second verse, the skipper explains how he envisioned himself as an A-lister who would be getting phone calls from Pulp Fiction director Quentin Tarantino and posing for Rolling Stone photographer Annie Leibovitz.
  
  In the third verse, he recalls when critics dubbed him "the new Olivier." Lawrence Olivier was a celebrated stage and film actor who was known for his powerhouse performances in Shakespearean plays like Richard III, Hamlet, and King Lear.
• The would-be star also insists his life would be different if he could have landed roles in Twelve Angry Men and Speed-The-Plow. The former is a courtroom drama that was a hit play and classic film; the latter is a satirical play by David Mamet about the American movie business.
• This was the third single from Alpocalypse, Yankovic's 13th studio album that also featured the Lady Gaga parody "Perform This Way."
• The album was nominated for Best Comedy Album at the 2012 Grammy Awards but lost to Louis C.K.'s Hilarious.