Born on September 14, 1964 in Hooksett, New Hampshire, Jamie grew up with a big Irish family. He is the youngest of six children and his father was a pilot during World War II. He attended Manchester Central High School during his teenage years. Taking advantage of an R.O.T.C. scholarship from Boston University, he left New Hampshire for good. From then on, he served for the U.S. Navy for five years, and consequently was able to go to different parts of the world. Thereafter, he became a bartender and eventually stumbled upon the world of comedy and acting. He later became a member of the Los Angeles's Acme Comedy Theatre Main Company.
Jamie Kaler has been seen on numerous television shows as a guest star. Some of his credits include appearances on The Late Late Sow, Friends, Monk and Will and Grace. The stand up comedian has also been known for lending his voice to the stop-motion animated series Robot Chicken, playing a suicidal blooper host. He began his career by acting on shows like Saved by the Bell: The New Class, JAG and Suddenly Susan, and portrayed a bartender on the 1998 film The Party Crashers. During the early 2000s, he was cast in a number of films. He voiced a character in Carnivale, played a manager in Welcome to Hollywood, was seen on the short Dodgeball and portrayed a character on The Tag. This was followed by appearances on 3rd Rock from the Sun, The King of Queens, Grounded for Life and Married to the Kellys. After being cast as a guest on the series Arrested Development, he worked alongside Adam Sandler, Tea Leoni, and Paz Vega on the romantic comedy Spanglish. Kaler was also seen on two films in 2005, namely Underclassman and The Family Stone with an ensemble cast. He later landed the regular role of Mike Callahan on the TBS series My Boys.