|Ray in Alaska in "Recovering Pessimist"|
|Air Date||February 28, 1997|
|Preceded by||The Game|
|Followed by||The Dog|
Recovering Pessimist is the 18th episode of Season 1, and is episode 18 of the full 210 episodes for the entire series. In this episode, Ray is nominated for Sportswriter of the Year. And even though that's a good thing, Ray, being the pessimist he is, knows that bad things are coming soon.
- Episode Title: Recovering Pessimist
- Episode Number: Season 1, Episode 18 (#18 of 210)
- Air Date: February 28, 1997
- Episode description (from DVD): "Ray wins the Sports Writer of the Year Award, but thinks that all this means is that something bad now has to happen to him. When Frank and Marie are unimpressed, Ray realizes that his pessimism comes from his parents."
- Preceded by: "The Game"
- Followed by: "The Dog"
Ray gets a letter in the mail from the editor of his newspaper. Apparently his editor nominated him for the Federated Press Association "Sportswriter of the Year" Award. Ray is reluctant to go to the awards dinner for fear that he will lose. He doesn't want to get his hopes up because he doesn't want to end up disappointed. But Debra convinces him to go.
The nominees for the award were Bill Scheft from the Boston Globe, Chuck Heaton from the Cleveland Plain Dealer, Ted Stankovich from the Chicago Tribune, and Ray Barone from New York Newsday. Ray always said that Ted was a hack. Chuck's big story that year was "Too Much Violence In Boxing". And Bill has already won the award twice. Ray's chances of winning were pretty good.
As it turns out, Ray did in fact win the award.
When he brings home the Sportswriter of the Year trophy, Ray is depressed. He knows that because this good thing happened to him, there's something bad waiting for him. Debra then questions why he's so pessimistic about everything. Ray explains that he doesn't want to be disappointed. She tries her hardest to get him to think optimistically. And Ray tries...
The next day, Ray's editor gives him a promotion, which is good but it means more work and responsibility for him. Then his parents are unimpressed with his award. Then he comes back home to find out that his editor wants to send him to Alaska for a few weeks to cover the Iditarod. After all of that, Ray is finished being optimistic.
This is one of many episodes in which Ray's good news greatly overshadows Robert's.
One of the nominees for the Sportswriter of the Year Award is Chuck Heaton from the Cleveland Plain Dealer. This is actually based on "real life". Actress Patricia Heaton's father is named Chuck Heaton and was a sportswriter for the Cleveland Plain Dealer. The writers took that true fact and inserted it into the script.
Another one of the nominees for the Sportswriter of the Year Award is Bill Scheft, currently a writer on the Late Show with David Letterman. Both shows are produced by Letterman's Production company, Worldwide Pants Incorporated.
- Ray: (talking about his side of the bed) "I took the side away from the door in case the boogieman comes in."
- Ray: "Alright, I'm a little pessimistic, but I got it under control, okay? I can be optimistic any time I want to."