Sean Hayes as Jack McFarland: Will's other (and first gay) best friend since college. Jack is flamboyantly homosexual, confident, and free-spirited, having been so from a young age. He drifts from man to man and changes occupations often, being very fickle when it comes to both.
He has worked as a struggling actor, an acting instructor, a back-up dancer for Jennifer Lopez and Janet Jackson, a sales associate at Banana Republic and Barney's department store, a cater-waiter, a student nurse, Junior VP for Out TV, and host of his own Out TV talk show, called Jack Talk. Jack made four one-man shows (called Just Jack, Jack 2000, Jack 2001, and Jack 2002) to showcase his singing/dancing/acting abilities; all attempts only having marginal success. Early on in the show he establishes a close friendship with Karen; the pair often spend time together and orchestrate various pranks. Throughout the series, Jack relies on Will and Karen for financial support. His idol is Cher.
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Classic TV. Just classic.