Cheatin' Trouble Blues is the 19th episode of the fourth season and 90th overall.
George and Marilyn's anniversary
Will and Grace head up to the Rainbow Room for a celebration of the anniversary of his parents, who come in kissing and cuddling happily. This makes Will happy and conclude his father George has ended his affair with his mistress Tina.
After giving his parents tickets to a South Pacific cruise, George asks if he can bring along Tina. At the same time, Grace finds out that Marilyn has also been having an affair with her yoga instructor Tim (who is not short for anything).
Will confronts them both at the dinner table and asks them to think things over. Grace advises Will that if that kind of set up is what makes his parents happy, he should just leave them be. Later that evening, George and Marilyn decide to separate.
Karen and elevatorsKaren refuses to ride the elevator because of a traumatic experience so she and Jack start to climb 80 flights of stairs. More than halfway, Jack realizes he left the cake they were supposed to bring for George and Marilyn's anniversary celebration on the 21st floor so they go back to retrieve it, exhausted.
Annoyed that they must climb all the way back up again, Jack asks Karen why she doesn't ride elevators and Karen begins to tell a story about her and her office mates being stuck on an elevator, being rescued by Keanu Reeves and threatened by Dennis Hopper to blow up a bus--scenes from the film Speed.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Shelley Morrison (Rosario Salazar)
- George is still seeing her mistress Tina and Marilyn has taken on an affair of her own with her yoga instructor Tim.
- Will reveals one of his brothers, presumably the eldest Sam was conceived on their parents' honeymoon.
- In Will on Ice, it was established that Grace is an avid fan of figure skating including Olympic figure skater Michelle Kwan. However she does not seem to show excitement that George and Marilyn are going on a cruise with Kwan teaching skating lessons.
- When Karen tells the story of her fear of elevators, she tells the opening scene of Speed (1994) where Keanu Reeves saves people trapped in an elevator right before it collapses. She also recalls thinking "Speed" was a film about amphetamines, alluding to the drug of the same name.
- Grace blames the show Sex and the City for popularizing fashionable but uncomfortable shoes for women.
- Jack asks Karen to do Liza Minnelli's pose during her Liza with a Z concert because of Karen's shiny outfit.
- Marilyn mentions burning her bra as a feminist statement during the 60s as part of the second wave of the feminist movement.
- Grace alludes to the film When Harry Met Sally (1989) when she describes Marilyn's braless experience as "When Hairy Met Saggy".
- After finding out his parents are having affairs, he describes them as Fleetwood Mac, the British-American band whose members has had extramarital affairs while on tour, including vocalist Stevie Nicks and Mick Fleetwood.
You're having an affair with a guy named Tim? What does he wear, a propeller hat? — George
I've always wanted to go on a cruise, and you know your mom likes any excuse to take anti-nausea medication. — George, receiving cruise tickets from Will