Sex, Losers and Videotape is the 19th episode of the fifth season and 117th overall.
Karen, Will, and his boss Mr. Stein find console in their failed romances. Jack helps Grace prepare a sexy video tape to send to her husband in Africa.
Synopsis[]
Lonely Hearts Club[]
A toast... love stinks!
Will is still sulking over how his feelings for Barry were not returned, so his boss Mr. Stein take him out for drinks to make him feel better. Karen joins them and they bond over how much love made them miserable.
However, as Will continues to push their anti-love agenda, Karen and Mr. Stein begin to connect and start a relationship behind Will's back. When Will eventually finds out about it, he feels more embittered. Later at home, he shares to Grace how he feels he can no longer share things such as heartbreak with her because she is in a stable relationship now. Grace reassures her that she will always be a loser, and offers to stay at his apartment for the mean time.
Grace's Sexy Video[]
Grace borrows Will's apartment to film a sexy video to send to her husband Leo in Africa. While Grace attempts to be sexy in front of the camera, Jack sees her and tells her she is trying too hard. He invites her to attend his acting class to help her lose inhibitions and get in touch with her sexuality. The class proves to be too humiliating for Grace so she storms off.
Later, Grace catches Jack videotaping her in the shower. At first disgusted, Grace eventually realizes that she looks sexy in the video because she is free and uninhibited and decides to keep the tape for her own. She and Jack later plan for him to sneak into Will's apartment again and "secretly" videotape her again in the shower.
Cast[]
Main[]
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
Guest[]
- 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)
Notes[]
- Mr. Stein's final appearance.
- The title of the episode is a reference to the 1989 Steven Soderbergh film sex, lies, and videotape.
- Grace mentions that she was thinking of actors Alec Baldwin and Dennis Quaid hooking up. Baldwin would appear in later seasons as Malcolm Widmark.
Cultural references[]
- Will compares Grace's leather trench coat to that the main characters of the techno-action film The Matrix (1999) wore.
- On her videotape for Leo, Grace sings Donna Summer's Love to Love You Baby (1975), which Beyonce would sample a year later on her hit Naughty Girl (2004).
- Karen claims she had been dumped by "one-ton billionaires, heads of state", and every member of the folk supergroup Crosby, Stills, Nash, referencing her prolific sex life with celebrities in the 1970s. This is mentioned again in The Definition of Marriage.
- Angry at Karen and Mr. Stein's relationship, Will remarks that when he builds his ark, "everyone's gonna get on one by one. Single file, no talking!",. This is a reference to the biblical story of Noah's Ark where all people and at least a pair of each animal (for mating) were saved in the ark.
Media[]
Quotes[]
I want you to go help Short Margaret with her depositions and Black Margaret with her appeal. They're in over their heads, especially Short Margaret. — Mr. Stein
I just had a great idea. Let's go to the video store and take all the romantic comedies and put them in the science fiction section. — Will
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