The second season of Will & Grace premiered on September 21, 1999, and concluded on May 23, 2000. It consisted of 24 episodes. Cast and characters Main cast Eric McCormack as Will Truman Debra Messing as Grace Adler Megan Mullally as Karen Walker Sean Hayes as Jack McFarland Recurring cast Shelley Morrison as Rosario Salazar Tom Gallop as Rob Leigh-Allyn Baker as Ellen Marshall Manesh as Mr. Zamir Gregory Hines as Ben Doucette Jo Marie Payton as Mrs. Freeman Special guest stars Debbie Reynolds as Bobbi Adler Veronica Cartwright as Judith McFarland Stone Phillips as himself Sydney Pollack as George Truman Al Roker as himself Molly Shannon as Val Bassett Neil Patrick Harris as Bill Orson Bean as Professor Joseph Dudley Piper Laurie as Sharon Joan Collins as Helena Barnes Guest stars Shirley Prestia as Mrs. Pressman Lou Cutell as Mr. Arthur Pressman Scott Patterson as Donald Dorio Peter Paige as Roger O'Neil Gary Grubbs as Harlin Polk Steve Valentine as Kai Tamlyn Tomita as Naomi Penn Badgley as Todd Megyn Price as Claire Laura Kightlinger as Nurse Sheila Markus Flanagan as Dr. Loranger Corey Parker as Josh Mary Pat Gleason as Sally Chris Potter as Michael Dan Bucatinsky as Neil Jennifer Elise Cox as Nurse Pittman Debra Mooney as Sister Robert Daryl Sabara as Broccoli Boy Episodes Note: the episodes on the Season 2 DVD are not in the same order as the broadcast dates shown below. References 2 1999 American television seasons 2000 American television seasons Television episodes directed by James Burrows