(2002-2003) Will Truman (Eric McCormack) is a gay lawyer and Grace Adler (Debra Messing), an interior decorator and neurotic single straight woman, is his best friend and confidante in the hit sitcom, who decides to have a baby this season -- and wants Will to be the father. Sean Hayes plays Will’s friend Jack and Megan Mullally is Grace’s utterly self-absorbed pal Karen, an uber-rich high-society horror whose husband goes prison for tax evasion. Harry Connick Jr. makes his first appearance as Dr. Leo Markus this season and guest stars this season include Kevin Bacon, Gene Wilder, Katie Couric, Elton John, Andy Garcia, Minnie Driver, Demi Moore, Nicollette Sheridan, and Madonna.