I remember that the opening scene of the pilot where Will and I are on the phone talking about George Clooney on ER and how we both found him handsome. The way it was written was so subtle that they did testing afterwards and half the audience didn’t realize at the end of the pilot that Will was gay. And that was considered a good thing for the show. They wanted the show to have legs and they knew they would have to capture the audience’s heart through the laughter first.”
— Debra Messing discussing response to the pilot of her groundbreaking sitcom Will & Grace with Huffington Post Live
I liked that concept about Will early in the series. Unfortunately, after a few seasons, show runners decided that it would be funnier if Will started acting more like Jack. So he started doing things like obsessively listening to Barbara Streisand, writing fan mail to Justin Timerblake and following celebrity teen feuds that were in the news at the time like Lindsey Lohan vs. Hillary Duff. There was even an episode where he tried to manipulate a friend into selling his bookstore so it couple be turned into a gym. Will would have never done those things in the first few seasons.
Falling back on stereotypes isn’t funny. It’s lazy writing.