S2, E5: When Grace (Debra Messing) joins her father (guest star Robert Klein) on a road trip, a secret from her past is finally revealed, causing father and daughter to address something that will change their relationship forever. Meanwhile, Will (Eric McCormack), Karen (Megan Mullally), and Jack (Sean Hayes) celebrate Jack's engagement at a gay bar run by legendary drag queen Miss Coco Peru (Clinton Leupp). When it's revealed that Jack has chosen both of them to be his best man, Will and Karen have a lip-sync monologue throwdown to determine who truly deserves the coveted title.