Originally the duo of Markowitz with childhood friend Obey City (Samuel Obey) was called ‘Hoodie Allen’ where he contributed to vocals and Obey City on production. Bagels & Beats EP and Making Waves mixtape marks the first two releases of the duo that earned them a MTVU's Best Music on Campus Award nomination in 2009. After Obey City stopped producing for the duo in 2010, Markowitz adopted Hoodie Allen as his stage name and continued to make music with RJ Ferguson.
Following his graduation from the University of Pennsylvania with a degree in marketing and finance in 2010, Markowitz took a job at Google in the capacity of an AdWords associate in the company’s Standardized AdWords Reseller Training (START) program. He worked full day at Google and after returning home at 6 pm devoted his time in writing songs, replying to fan emails, and scheduling concerts until 2 am or 3 am. He later left the Google job to concentrate fully on his music career.
He heavily sampled the song ‘I Am Not a Robot’ by Welsh recording artist Marina and the Diamonds in his debut single ‘You Are Not A Robot’ in June 2010. It clinched the top position on ‘Hype Machine’.
He then completed the mixtape ‘Pep Rally’ by September 2010 that sampled songs from ‘Two Door Cinema Club’, ‘Ellie Goulding’, ‘Marina and the Diamonds’, ‘Flight Facilities’ and ‘Death Cab for Cutie’. ‘You Are Not A Robot’ became lead single of the mixtape. A self-financed video of the single led the mixtape to get downloaded for more than 200,000 times.
Since March 3, 2011, he has featured in four videos with the comedy website CollegeHumor's team Jake and Amir.
His next mixtape ‘Leap Year’ that released in July 2011 garnered decent popularity reaching 250,000 plays in SoundCloud in its first week of release. He headlined a 15-city tour in North America including in New York City and San Francisco to back the album. During the week of August 5 that year, Markowitz was #2 on Billboards Uncharted Territory.
He declared through Twitter on March 4, 2012 that his forthcoming debut EP would be titled “All American’. The first single of the EP titled ‘No Interruption’ and its music video was released by him on March 29 that year. The music video that was uploaded on the same day has till May 1, 2018 garnered over 34 million views.
On April 9, 2012, the music video of the second single of ‘All American’, titled ‘No Faith In Brooklyn’ featuring Jhameel was released. The EP ‘All American’ was released on the following day. It debuted as the #1 album on iTunes and #10 on the Billboard 200 with a first week sale of 28,000 copies. During April and May 2012, he made a 22-stop tour in the US featuring several artists including rapper Wax and Jared Evan to promote the EP. On April 19, 2012, he officially declared through Facebook the four dates of a "UK tour for June”. The ‘I Work Better In The UK Tour’ marked his first overseas performance.
After the success of ‘All American’, Markowitz released ‘Crew Cuts’ on February 20, 2013 that was marketed as “the free album”. It consists of eleven tracks including instant classics like ‘Fame Is For Assholes’ featuring Chiddy and ‘Two Lips’ featuring Moosh & Twist.
His performance on his new non-album single ‘Make It Home’ with Kina Grannis on Fuse TV was released nationally on April 30, 2013 on Fuse TV as also on Markowitz’s YouTube channel. Its studio version that released on May 15 that year on iTunes positioned itself among the top 10 of the iTunes Hip-Hop/Rap charts. Other non-album singles of the artist includes ‘The Moment’ featuring Travis Garland and ‘Let It All Work Out’ both of which released in 2015.
He came up with the music video for ‘No Interruption (Acoustic)’ on July 30, 2013 and on August 13 that year he self-released the acoustic EP titled ‘Americoustic’. The EP reached atop the Hip-Hop/Rap album chart and at #4 on overall albums chart on iTunes.
He self-released his debut studio album ‘People Keep Talking’ on October 14, 2014 which was made available to stream via iTunes First Play earlier on October 7 that year. The album consisting of 14 tracks peaked at #2 on iTunes on the albums chart; on the US Top R&B/Hip-Hop Albums (Billboard) chart; and on the US Top Rap Albums (Billboard) chart. It also marked his first work that released via physical CDs.
He promoted release of ‘People Keep Talking’ by performing one of its tracks titled ‘All About It’ on Good Day Philadelphia. He also did a world tour, the ‘People Keeping Talking World Tour’, from October 29, 2014 to sometime in June 2015 to promote the album. The tour covered venues in the US, Canada, Australia and Europe featuring artists like MAX and Chiddy.
His second studio album ‘Happy Camper’ was released on January 22, 2016. In spite of being released for free, the album that was also made available for iTunes download peaked at #2 on the overall albums chart.
He released his third studio album titled ‘The Hype’ on September 29, 2017. It includes tracks like ‘Know It All’ and ‘Ain't Ready’.