Today in TV History: Debra Messing’s Favorite ‘Will & Grace’ Episode Featured a Water Bra

Of all the great things about television, the greatest is that it’s on every single day. TV history is being made, day in and day out, in ways big and small. In an effort to better appreciate this history, we’re taking a look back, every day, at one particular TV milestone. 

IMPORTANT DATE IN TV HISTORY: November 2, 1999

PROGRAM ORIGINALLY AIRED ON THIS DATE: Will & Grace, “Das Boob” (Season 2, Episode 3). [Stream on Hulu]

WHY IT’S IMPORTANT:  A show like Will & Grace, currently seeing an improbable run of success in its resurrected 9th season, is bound to have many episode listed as people’s personal favorites. There are a handful of agreed-upon classics, yes, but the high points of the series are spread far and wide over the seasons (okay, mostly over the first four seasons. Your gay spelling bee episode might be my Thanksgiving road trip might be someone else’s Sound of Music singalong. But if you ask series star Debra Messing what her favorite episode of the series was, she’s quick with an answer: season 2’s “Das Boob,” where Grace acquires a water bra in order to enhance her profile when meeting an old flame. Per this interview (go to 4:30):

“To me,” Messing said, “that was the most broad we were, at least that I was involved in the eight years, and I felt like it was kind of a wink to Lucy and Desi. And it just was a perfect comic set piece.”

It’s a great episode. A classic sitcom premise — Grace’s photo ends up in the paper, and via a trick of lighting, the photo makes it look like she’s got “massive jugs” (per Jack), leading an old high school crush of hers to call her up and ask her out — gets elevated to madcap farce when Grace buys a water bra in order to maintain the illusion of knockers (The Illusion of Knockers is my favorite Sony Pictures Classics Oscar contender) and said water bra gets punctured by Karen’s brooch and starts shooting water clear across an art gallery. Will rushes over to help her cover, and things just get weirder from there. The busty eruption is only one of the several bust-focused gags in the episode, coming after a marvelously deadpan moment where Will, Grace, and Jack each grab a handful of each other’s chest.

“Das Boob” may not have reached the levels of classic Lucy and Desi, but the slapstick hijinks that happen after Grace’s hooters start leaking amount to one of the show’s most memorable moments. Debra Messing, as you might’ve guessed by her involvement with Smash, has very good taste.

Stream Will & Grace's "Das Boob" on Hulu.