S5, E22: Will (Eric McCormack) reluctantly opposes Karen (Megan Mullally) when he represents her husband while she hires a goofy, immature young man (guest star Macaulay Culkin, "Home Alone") who seems barely out of high school to argue her case - and Will takes pity on the pseudo-slacker. Elsewhere, Grace (Debra Messing) hires Jack (Sean Hayes) to temporarily replace Karen but finds she might have to choose between her friendship with him and a wealthy client (guest star Clark Gregg). Shelley Morrison also stars.