Born in Chicago, his comedy career began at the age of 19 while attending college in Florida. Toured as a road comedian until 2001 before moving to Los Angeles where he became the only white, Jewish comedian in LA's black comedy scene for nearly a decade. He became a writer for Katt Williams (2007). Williams referred to Lolli as the "Urban Jew". He was co-host of the PepTalks podcast and created content for All Things Comedy Studios (2018-2020) and writes for legendary comedian Eddie Pepitone. Lolli has his own weekly Podcast "The No Idea Zone" available on YouTube live and for download on iTunes, Spotify and I heart Radio.