His material often covers the comedy industry itself, criticizing other comedians for being too predictable. One of his more notable criticisms was that of Dane Cook where he compared the comedian's rise to that of Adolf Hitler's. He then went on to say that Cook was worse than Hitler, because at least Hitler had a point of view. Andy often criticizes his own comedy even in the middle of his act. If a joke doesn't do well he'll immediately start discussing why it didn't work with the crowd.
He played the character "Andy" a fellow sportswriter and friend of Raymond on the TV show Everybody Loves Raymond, is a regular guest on Late Show with David Letterman, contributor to The Daily Show, has performed on HBO and made numerous appearances on Dr. Katz and Home Movies. He is also known for his annual "State of the Industry" address at the Just for Laughs comedy festival in Montreal.
In 2010, Kindler was a judge on the stand-up reality show Last Comic Standing.
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