Das Boob is the 3rd episode of the second season and the 25th overall.

Grace gets a call from an old crush from high school after a magazine feature. Jack finds out Will messed around with one of his exes.


The Dynamic Duo

Ep 02 03-0-0

I think you sprung a leak!

After being featured in the local paper, Grace gets a call from her high school crush John Gregorio, wanting to meet up. Will and Karen imply that John only called because Grace's magazine feature includes a picture of her with deceivingly big breasts. Karen takes her to the store and makes her try on the hydra-bra ("water-filled for extra perkiness") that makes her chest appear larger.

At John Gregorio's gallery opening, Grace's bra is caught in Karen's brooch and gets punctured, squirting water all over. She tries to cover it as John talks to her but eventually comes clean and admits wearing it to impress him. John expresses disappointment in Grace's shallowness and walks away, only to bump into Karen and stare at her breasts.


John Gregorio

Slam the door, Jack

Jack finds an earring that belonged to Walter, whom he used to date on Will's couch, and finds out that Will "messed around" with him after their break-up. Jack then expresses consternation as he considers Walter the love of his life and was devastated when Walter dumped him. Feeling betrayed, he ignores all of Will's apologies.

Will finally gets Jack to come to John Gregorio's gallery opening under the pretenses that Cher, whom Jack idolizes will be there. Will also invites Walter to come so he and Jack can reconcile. However when Walter finallyarrives, Jack whispers to Will that he is actually mistaken and that he is thinking of another guy, not Walter, then runs away.





  • The title is a reference to 1981 German film Das Boot.
  • When this epsiode was repeated on December 13, 2001, John Gregorio's name was dubbed to "Donald Dorio" and the name and phone number on the wall were also changed, as well as the closed-caption text. However, Scott Patterson was still credited as "John" in the end credits. The Judy Lombardosi joke (Slutty Big Boobs) was also cut.
  • The Zelman Gallery is named after Debra Messing's then-husband, Daniel Zelman.
  • Debra Messing has stated in interviews that this is her favorite episode because being a fan of physical comedy, she describes it as "classic Lucille Ball", although she ended up sick in bed for two weeks for being soaking wet so long.[1] She submitted this episode to the 2000 Primetime Emmy Awards where received her first nomination for Outstanding Lead Actress in a Comedy Series.

Cultural References

  • Karen refers to Grace's breasts as the "dynamic duo", the name given to the Batman-Robin team up.
  • When Cher does not appear at the gallery, Jack exclaims that unless Will "can turn back time, I'm very very angry," referring to Cher's 1989 hit If I Could Turn Back Time. Cher eventually appears in Gypsies, Tramps and Weed and she and Jack sing the first line of the song.



Grace:John Gregorio called? Oh, my god! No way! He's such a fox!
Karen:Good lord. A pack of cigs and a pregnancy scare and this could be high school.
Will:Where have you been? I've been trying to call you all day.
Jack:Oh, what a coincidence. I've been trying to ignore you all day.

Okay, John, I'm going to be honest with you. We live in a deeply patriarchal society in which women are unfairly judged by--ugh! My boobies are fake. Gracecoming clean about her HydroBra


  1. Debra Messing Tells Us Her Favorite Will & Grace Episode Ever! Plus, Smash Scoop!
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