Sex, Losers and Videotape is the nineteenth episode of the fifth season and 111th overall.
Still nursing a grudge over his last failed relationship, Will forms a gin-soaked anti-romance club with other lovelorn losers -- his cuckoo boss, Mr. Stein, and Karen -- but the threesome shrinks dramatically when Stein takes a shine to the ever-ready Karen. Meanwhile, Jack sneaks a video camera into Grace's private boudoir and records her privates -- and posterior -- for posterity.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Gene Wilder (Mr. Stein)
- Emily Rutherfurd (Joanne)
- Matthew McCray (Jasper)
- Charles C. Stevenson Jr. (Smitty)
- Erin Fritch (Young Woman)
- Kevin Sizemore (Young Man)
- Kari Lizer (Connie)
- Jon Fleming (Russell)
It's just that he's someone I could really see having a future with. I wanted to come home to him every day and say, "Hey, honey, what's for dinner?" And he'd say, "I don't feel like cooking. Let's go out." And I'd say, "We always go out. Put down the scotch and pick up a whisk. Why are you crying now?!" It's not sexy, but it's what I grew up with. — Will, about Barry