Bobby's life story began in Rochester, New York, where he was born, before his family relocated to Margate, Florida, a suburb of Pompano Beach, when he was just seven years old. This significant move had a profound impact on his early life, shaping his experiences and opportunities to come. As a result of his family's relocation, Bobby spent his formative years in Margate, Florida, where he became an integral part of his school community, actively participating in various extracurricular activities and earning the rare honor of being inducted into "Who's Who Among American High School Students."
Following his high school years, Bobby attended Cornell for two years before transferring to Florida Atlantic University, where he graduated with a Bachelor of Science degree in Communications. His first professional job was as a video editor in the sports department at WCIX Channel 6 in Miami, Florida. This experience laid the foundation for his future career, as he went on to work as a news editor, producer, and part-time reporter at WPEC TV 12. During his time at WPEC TV 12, Bobby had the privilege of interviewing a diverse range of notable figures, including Sugar Ray Leonard, Billy Jean King, the New York Yankees, and the rock group Kiss.
In addition to his work in television, Bobby also pursued his passion for comedy, selling his first jokes to comedian and impressionist Fred Travalena while working at WPEC TV 12. His stand-up comedy skills were further showcased when he won "The Gator Laugh-Off," a stand-up comedy competition sponsored by a South Florida radio station. This success led to him moving to the Midwest to work in radio as a morning show personality at KJEZ, "The New Z-95." During his time at KJEZ, Bobby's comedic talents were showcased on the number one morning show, "Mr. Robby in the Morning," for which he won several "Silver Microphone Awards."
After two years of success in radio, Bobby decided to pursue his stand-up comedy and acting career, moving to the West Coast to pursue his dreams. He has since appeared on various television networks, including Comedy Central, "E," and The Style Network, as well as in independent films.