Winston Shakespeare
Movie character
11
MENTIONS
2
EPISODES
2
PODCASTS
Search complete. 11 mentions across 2 episodes found for "Winston Shakespeare".
Oct 6, 2026
DaveHOST
Yeah.
DaveHOST
And on the island, she meets a guy called Winston Shakespeare, right? She meets
DuncanHOST
a guy called Pepe who plays
DaveHOST
guitar.
DaveHOST
No, no. Winston Shakespeare, who is the local shagger, basically.
DaveHOST
And 20 years younger than Stella.
DaveHOST
Now, it doesn't take long before they start a hot and steamy romance.
DuncanHOST
never seen this movie, and now I kind of will watch this movie, and I will be so disappointed if she doesn't choose... family-in job over Jamaican penis.
CJHOST
Mm.
JasonHOST
Our boy, uh, Winston Shakespeare.
CJHOST
Yes, sir.
JasonHOST
Taye Diggs.