...And the Horse He Rode in On is the 1st episode of the fifth season and ninety-third overall.

The episode marks the first appearance of Harry Connick, Jr. as Leo, and Stanley's return from being in prison since season 4 episode Crouching Father, Hidden Husband.


The Jewish doctor

Picking up from the last scenes of Season 4, Grace wakes up after hitting her head on the way to be inseminated at the fertility clinic. A man in a horse helps her up and introduces himself as Leo Markus, a Jewish doctor. He treats her head wound and gives her a ride to the clinic where Will has been waiting.

Grace bumps into Leo again at the coffee shop and asks her out again but she declines and accidentally leaves her wallet. Leo drops it off later at her apartment with a note and his number.

Everything but

Stanley comes home.

Stanley comes home.

With her husband still in jail and a standing invitation from Lionel Banks, Karen reluctantly goes to Lionel's hotel suite where according to her, they did "everything but". She resolves to stay faithful to Stan.

However that night, Karen has apparently decided to sleep with Lionel so Jack tries to stop her to keep her from getting hurt. She reassures him that he has nothing to worry about. While waiting for Lionel at her mansion, Stanley comes home.



  • Grace does her "whoa" reaction again.
  • Karen is once again referred to by her alias Anastasia Beaverhausen by Lionel Banks.
  • Jack is able to produce a sperm sample in 25 seconds.
  • Stanley's shadow appears when he comes home but he remains not seen.
  • Will kissed a guy as Pink's song Get the Party Started (2001) played at the Gay Gay Gay Gay Gay club.

Cultural references

Leo silhouette

Differences between Leo's silhouette seen in season 4 finale and season 5 premiere, the latter of which features Harry McConnick, Jr.

  • Leo's introduction and the title of the episode is a play on the phrase "and the horse you rode in on". It alludes to the fact that he is Grace's "knight in shining armor" similar to fairy tales, riding a white stallion and saving her from distress.
  • Jack suggests Will have his baby with All My Children actress and talk show host Kelly Ripa.
  • Karen refers to courtroom reality show Judge Judy.


Jack:Come on, Will. Put your lips on, fix your wig, 'cause we are going to the new club called the Gay Gay Gay Gay Gay Club.
Grace:Aw, that sounds fun. Will you take me sometime?
Jack:Grace, please, it's not that gay.
Inviting Will to go out

What are you talking wrong? You're the one who told me monogamy was for lesbians. Karento Jack trying to stop her sleeping with Lionel

That delicious scent... I knew it either had to be you or a thousand wild gardenias nestled in a mossy bank of money. LionelKaren's scent

Jack:Come on, Will. I'm all set. Even got my surprise underwear on.
Will:You mean no underwear?
Jack:That's the surprise!

Sex is a drug, Karen. I should know. I'm a licensed dealer. Jack

Will:It's been this way for generations. Moms stay home. Dads go out and cruise guys.
Jack:Or as my dad used to call it, "bowling."
To Grace as they were going out



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