Jon Manfrellotti's wry sense of humor and impeccable timing greatly contributed to his successful comedic career. He first made his mark as a stand-up comedian in Florida and then New York City, before shifting gears into television and film acting. Manfrellotti had a recurring role on the Emmy Award-winning sitcom "Everybody Loves Raymond" (CBS, 1996-2005), which starred Ray Romano as a sports writer who struggles to keep the peace within his wacky family. He played Romano's best friend who is always getting on the nerves of his bossy wife. Manfrellotti reunited with Romano on the comedy-drama "Men of a Certain Age" (TNT, 2009-2011), where he played a bookie who tells endless jokes to deflect his insecurities. On the latter series, he easily won over critics and audiences for his honest portrayal of a man who looks rough and tough on the outside, but who is secretly longing for real companionship. Manfrellotti stole practically every scene that he was in, showcasing his expertise in balancing complex emotions without losing his comedic edge.