Songfacts®:

• This song tells the fictional story of a 19-year-old guy named Jimmy who leaves his girlfriend to enlist in the military. He is killed by another soldier two weeks before his 20th birthday. The lines "There's still no shame from the man to blame" and "There's still no shame, and we're all to blame" show how much war affects the people involved.
• Printz Board, known for his work with the Black Eyed Peas, played the trumpet on this song.
• Yellowcard bassist Pete Mosely discussed the tune with Caught In The Crossfire: "It's the story of a G.I, it's got some anti-war sentiment in it, but it's not as openly political like – say – Propagandhi. It's very non-specific. It doesn't name names or point fingers, but it relates to an aspect of the American Armed Forces that I disagree with – the way they use cheap tricks to recruit kids out of high school. We're talking about kids that might not have the grades or money to move on to university, so the Forces come along and offer them this 'educational experience, get you ahead in life,' that kinda thing, and the kids often sign up for it – not really knowing that they'll end up going to war.
  
  In the song, Jimmy is a kid from a typical industrial town in New Jersey, who probably has a future working in a local factory ... but the factory gets shut down, so he has to take the only other opportunity he sees as available to him, and ends up going to war and dying at a young age. So it's not so much a song about war, as how it impacts on the lives of a young soldier and his family."
• Yellowcard frontman Ryan Key weighed in on the song's significance in a Rolling Stone interview. "That stretched the limits for us," he said. "It's this jazz-lounge anti-war song. You're listening to this super-smooth, jazzy groove, but we're talking about something that means a lot to us - and that's really cool. It's more intense subject matter than we've ever tried to tackle."
• The song is part of Yellowcard's 2005 album Lights And Sounds, the follow-up to their highly successful major-label debut, Ocean Avenue. "Two Weeks From Twenty" shows an evolution in their sound, with jazz influences and a more restrained delivery. Sean Mackin, the band's violin player, shows off his classical training on the track.