Will & Grace’s most iconic moments: Four classic episodes that gave us life lessons
After breaking up with boyfriend Nathan (Woody Harrelson), Grace is balled up in bed, refusing to eat or come out of her room. When Karen asks how bad she is, Will says she’s “Mariah Carey in Glitter”.
Yet when their attempts to cheer up Grace fail miserably, Will knows how to reach out to her: a heart-to-heart chat where he learns to let Grace decide how she wants to grieve.
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Of course, he also makes her dig out the childhood photos she loves to pore over. By the end of the day, Will, Jack and Karen are asleep in her bed, exhausted from her stories, and Grace gets over her broken heart by seeing her friends‘ full ones.
GRACE ADLER: EMBRACE YOUR INNER CHILD
SEASON TWO, EPISODE THREE: “DAS BOOB”
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Sure Grace is ditzy, but the fact that she embraces childish fun makes her all the more loveable.
Will & Grace has delivered lots of side-splitting sight gags, but they don’t come more childishly hilarious than in “Das Boob” – the episode in which Grace wears a water-filled “hydra bra” to impress her high school crush John Gregorio (Scott Patterson) at his gallery opening. What could possibly go wrong?
When Grace snags the bra on Karen’s brooch, of course it leaks, right in front of John – and all over his artworks. Debra Messing has said this 1999 episode is her all-time favourite.
KAREN WALKER: PUT A BUDDY DOWN TO LIFT THEM UP
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SEASON TWO, EPISODE 15: “ADVISE AND RESENT”
No-one throws shade like Karen throws shade, but the insults she directs at Grace (and Will and Jack) always come from a place of love – harsh love, yes, but love all the same.
There are countless examples of when Karen used an acerbic one-liner or two to lift her friend’s spirits – or to simply deliver a truth bomb.
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When in this episode Grace arrives at work in a cow-print skirt, Karen simply raises an eyebrow and says, “Woah. Got skirt?” It’s a smart reference to the US “Got milk” advertising campaign that ran for almost 20 years – and we’re almost certain Grace never wore the statement skirt again.
JACK MCFARLAND: NEVER MEET YOUR IDOLS
SEASON THREE, EPISODE SEVEN : “GYPSIES, TRAMPS AND WEED”
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Jack’s obsession with singer and actress Cher is a theme throughout the show, but when he finally encounters his idol in person in a restaurant, he doesn’t believe it’s her.
“I don’t think I need a drag queen to define normal behaviour,” he tells the real Cher. He then goes on to out-Cher Cher by trying to school her in Cher’s correct mannerisms and phrasing.
He comes to his senses only when Cher slaps him and walks away. If ever there was proof that it’s probably better that you never actually meet your idols, this episode delivers the lesson. We bet Jack wishes he could turn back time.
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