...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. As he treats Grace's head wound and gives her a ride to the clinic where Will has been waiting, Leo asks Grace on a date but she politely turns him down, given her situation with Will and the pact they made to stop dating for a while and focus on starting a family together.

Serendipitously, Grace bumps into Leo again at the coffee shop and he asks her out a second time. Grace, again declines the offer, but accidentally leaves her wallet behind. Leo drops it off later at her apartment with a note and his number. Grace, after learning that Will had kissed another man somewhat breaking their pact, starts to think of giving Leo a chance.

Everything but

Stanley comes home.

Stanley comes home.

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

However, later 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, Karen is dumbfounded to see Stanley come home.


Main Cast



  • 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.
    • In this scene, Karen sees Stanley while waiting for Lionel. However, in the next episode she claims that Lionel had already arrived before Stan and that she had to signal him to get out using one of her breasts.
  • 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.



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 from having an affair

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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