I am doing some imdb based research on the careers of these two actors, and finding that the success of their romantic interest/lead actress co-stars are quite different from each other.
Take into account the early actresses in both comedy variety born stars movie careers:
Billy Madison and Happy Gilmore: Can you remember the name of the actress form either of these films? Or what they've notably been in lately?
Ace Ventura Pet Detective: Co-star actress.... Courtney Cox. This movie was released the same year Friends started. No need to mention the success of that show.
The Mask: Newcomer Cameron Diaz co-stars with Carrey in this film as his love interest. Goes on to have huge career.
Next up for both, the prove yourself-as-an-actor-more-serious-roles.
Actually this phase took longer for Sandler. He follows up with The Wedding Singer, Big Daddy and The Waterboy.
Co-star victims: Drew Barrymore, Faruiza Balk, Joey Lauren Adams. Drew has been stuck playing the same role she did in Wedding Singer ever since, Faruiza just got ugly and Adams only gets a job when Kevin Smith calls.
Carrey's works: Truman Show Man on the Moon, Me Myself & Irene.
Co-stars: Laura Linney(automatic win), that bitch that nothing can be done for and Renee Zellwegger.
Look at Renee's career post-Carrey in comparison to shipwreck of Sandler's better halves. Oscars, Oprah and major roles.
Either there's something to this or I'm really bored.