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How to Succeed in Business Without Really Crying is the 5th episode of the ninth season and 199th overall. Karen's rival Beverly Leslie returns since his "death" during the season 8 finale.

Will and Grace are poised to advance into their respective careers. Karen finds out someone else is staying in her suite at the club. Jack wins half of a lottery prize.

Synopsis

No surprises

Will is up to be senior partner in his firm and is feeling contented that if he gets promoted, he would know how the rest of his life will be like. Grace is excited as well, as she is set to meet up with an affluent business owner.

During the meeting, Grace learns that her client is interested in Will so she asks her best friend if he would be interested in hooking up with him so she could get the job. At first furious, Will agrees after he realizes that Grace's client with is the "power gay" Eli Wolff, the successful owner of a chain of boutique hotels.

However, after meeting with the other senior partners of his firm, Will realizes that he does not want to be a corporate lawyer for the rest of his life and uncontrollably sobs in the middle his date. Eli walks out and Grace is worried that she might lose him as a client.

Later, Grace finds out that Eli did give her the job but also realizes that she had been insensitive to Will's problem during the entire situation. To make it up, Grace asks Will to quit his job and proposes that they run their business together, to which he happily agrees.

Beverly's secret

Karen's frenemy Beverly Leslie is recovering from surgery and while still under the heavy medication, confesses to Karen that he is gay and asks for help coming out his wife Crystal in exchange for the hotel room they are both fighting over.

After the drugs have worn off, Beverly could not remember his confession and insists that he is not gay. Karen gets her revenge by telling Crystal she should make love to her husband "from the front".

A real Mexican stand-off

Jack is excited that he is getting half the prize of a winning lottery ticket that his colleague Theodore bought with Jack's money. However, Theodore only gives him a dollar as payment for the ticket. The two of them ended up giving the money to help Tasha's father fix the car he is using as a Lyft driver.

Cast

Main

Guest

Notes

  • Title is a reference to the musical and book How to Succeed in Business Without Really Trying.
  • First appearance of the new Benji. The last "Benji" appeared in the episode Cowboys and Iranians and was played by a different actor, though the actors are both black and bald.
  • Beverly Leslie holds Crystal's funeral in Birds of a Feather Boa. However in this episode, he reveals she is still alive because the "first shovel of dirt on the coffin revived her".
  • This is the second time Grace gets a job by setting Will up with his client. She first set up Will with the obnoxious publicist Nathan Berry in Saving Grace.
  • Will and Grace work together again since their apartment flipping business during season 4.

Cultural references

  • When Jack asks Will who is "gay, beautiful, and just got rich for doing nothing", he answers Jared Kushner, who serves as Senior Advisor to President Trump and is also his daughter Ivanka's husband.
  • When Jack talks about his employers Theodore and Alvin, Will asks about Simon and references Alvin and the Chipmunks characters with the same names.
  • Karen references the recent decision to tear down Confederate monuments specifically in Richmond, Virginia’s Monument Avenue after accusations of glorifying white supremacy.
  • Karen refers to Beverly Leslie as Dixie Dinklage after his Southern accent and actor Peter Dinklage, who was also born with dwarfism.
  • Jack tells Theodore that his story had conflict and drama, which is what TV producer and writer Shonda Rhimes calls "conflama."
  • Jeff Sessions
  • Karen makes a reference to the ongoing Harvey Weinstein sexual harassment allegations when she mentions producer Harvey Weinstein not being a complete gentleman.
  • When Grace walks in with her hair messed up, Will calls her "white Diana Ross", who had the same signature look in her later career.

Media

Quotes

Tell Masseur that I just played the front nine and need a back rub. Actually, tell him I played the back nine and need a front rub. Karen

Beverly:I'm not going anywhere. I've just had extensive plastic surgery.
Karen:Where? Oh, wait. Let me guess. Labia reconstruction?
Tony:I'm straight.
Eli:I'm listening.

I must have died during surgery, 'cause the devil herself is before me. Beverly Lesliemeeting Karen again

Beverly:Karen, this may come as a great shock to you. But I'm a... homosexual.
Karen:That's it? What's your next bombshell? Harvey Weinstein isn't always a perfect gentleman?
Theodore:Get out the way or I'll—
Jack:Or you'll what? You can't hit a gay man; it's a hate crime!
Jack:Gimme half that money or else!
Theodore:Or else hitting a black man is a hate crime, too. Rarely enforced, but still.
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