Born in Chicago, comedy career began at the age of 19 while attending college in Florida. Toured as a road comedian in 2001 before moving to Los Angeles where he found it impossible to break into the Hollywood clubs, leading him to into the underground Black clubs (2002-2011) when he was discovered by Katt Williams (2007) who referred to Lolli as the "Urban Jew". Presently, he is creating content for All Things Comedy Studios and writing for legendary comedian Eddie Pepitone.