Songfacts®:

• American singer-songwriter Andy Grammer was born in Los Angeles, but grew up in New York. His father is the singer-songwriter Red Grammer, who is best known for his children's music. At 20, Andy returned to the Los Angeles area, where he started his "professional" career as a street musician busking on the promenade in Santa Monica, California. It was there that he perfected his writing skills as an artist and he wrote this song to raise his own spirits after a particularly long day. Grammer explained to Alternative Addiction: "I had been out on the streets trying to sell my album, and this particular day I didn't really sell any. So I came home and wrote myself a little pick me up, which turned out to be 'Keep Your Head Up.'"
  
  The song proved to be more than a pick me up - it became his entry into the music industry. "My big break has been this song," said Grammer. "Once I wrote that song, people started to notice me as a musician. I went for accosting people while they were eating dinner to hopefully get their ear to driving around in a cab in New York City, heading to all the major labels."
• The interactive video stars Rainn Wilson from NBC's The Office. "Rainn Wilson is such a homie," Grammer told Spinner UK: "He co-wrote a book with my old roommate. One day he was in my apartment and I took him out to lunch and told him about the video and he was so gracious to be in it."
• When we spoke with Grammer in 2014, he talked about the benefits of street performing, explaining that it's hard to get real feedback from people who know you or come to your shows. When you have to get the attention of total strangers, it makes you up your game. "By the time my manager came and found me and things started to move, I'd been trained pretty intensely on the level of excellence that you need to actually serve someone's ears," he said.