Sex. Losers & Videotape

S5 E19: Still nursing a grudge over his last failed relationship, Will (Eric McCormack) forms a gin-soaked anti-romance club with other lovelorn losers - his cuckoo boss, Mr. Stein (guest star Gene Wilder, "The Producers"), and Karen (Megan Mullally) - but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen. Meanwhile, Jack (Sean Hayes) sneaks a video camera into Grace's (Debra Messing) private boudoir and records her privates - and posterior - for posterity.