Songfacts®:

• "Hail Mary" is the first full song Pomplamoose posted on YouTube, uploading it on July 6, 2008. It didn't go viral, but they got a lot of positive feedback and kept making more, building up their subscriber count along the way. By 2010, they had accumulated millions of views, with cover songs like "Single Ladies (Put a Ring on It)" and "September" getting the most attention. They became one of the few artists to actually make a living on YouTube, something many artists tried to do in ensuing years.
  
  It was all very satisfying for the Pomplamoose duo of Nataly Dawn and Jack Conte. He had a different, more traditional band that he put on hold to focus on Pomplamoose, and she was still a student at Stanford (where they met) considering a career in marketing or teaching French when she decided to give it a go.
• Pomplamoose called this a "VideoSong," which they described as one where you see everything you hear, so if a shaker comes in on a song, you see it. There are often different instruments and vocals going on simultaneously, so they developed an editing style where the screen splits into different sections to accommodate, which became their signature look. It was low-budget but they had great sound quality and good lighting, giving them an edge over just about everything else posted to YouTube at the time.
  
  During this time, Jack and Nataly did everything themselves, but their operation expanded a few years later and they started hiring others to help with the music and production. In 2017, they started releasing a video every week.
• In this song, Nataly Dawn sings in character as a ramblin' man who leaves his family, heading out to San Jose at 90 miles per hour. Dawn does write some personal songs, but she puts them out as a solo artist, not with Pomplamoose.
• The title has a religious meaning, as the Hail Mary is a Christian prayer. Nataly Dawn's parents were Christian missionaries, but she forged her own spiritual path.
• The video ends with a link to the Pomplamoose MySpace page where you could buy the MP3. This was the nexus when YouTube was making MySpace irrelevant for music.