Hoodie Allen originally was the duo of Steve Markowitz and Obey City (Samuel Obey, a childhood friend) on vocals and production, respectively. The name came about because Steven's nickname growing up was "Hoodie," and he wanted a name that "would stick in peoples' minds and be a little bit funny and representative of who I am" so a play off of famed filmmaker Woody Allen was settled on. Steve and Obey's first two releases were the Bagels & Beats EP and Making Waves mixtape. These earned Hoodie a nomination for MTVU's Best Music on Campus Award in 2009. The single "UPENN Girls" also received notable attention. However, in 2010 Obey City ceased to produce in Hoodie for unknown reasons, and Steve continued making music with RJ Ferguson (aka RJF), giving himself the name Hoodie Allen. In June 2010, he released "You Are Not a Robot," which sampled "I Am Not a Robot" by Marina and the Diamonds and which hit No. 1 on Hype Machine, an aggregator that collects the most-blogged about music in the world. After seeing the response, he spent the summer working, and finished his mixtape Pep Rally by September. The album was largely produced by RJF, and sampled songs from Death Cab for Cutie, Flight Facilities, Marina and the Diamonds, Ellie Goulding, and Two Door Cinema Club. He picked the name "Pep Rally" because he said that it "captured the energy of the record" and something "new and exciting. " He self-financed a video for the lead single "You Are Not A Robot," which helped the mixtape get downloaded over 200,000 times.