Michael is set up with Wendy

Episode
The Chair Model (Season 4, Episode 10)

Pranker
Kevin Malone

Target
Michael Scott

Description
Michael's break-up with Jan has left him desperate for a woman (don't worry, desperate situations yield the quickest results). His eyes wander to whatever smoking hot woman comes about, and that fantasy formulates with the desk chair model in this month's supply catalog. This leads him to go to his friends in the office, to come up with a friend of theirs to fix him up with, using the model as a template. He tries first with Kevin, who is looking more for himself than Michael. Then, he tries his luck with Oscar, who obviously has trusting women friends who have no worry about Oscar getting handsy. Phyllis interrupts and suggests her friend Sandy, who is not up to the Scott-rowboat-capsizing standard. Michael's dating search goes into a "formal" mode, and forces everyone to give a name of an eligible woman with the threat of being fired. Therefore, everyone goes to town on the cards. Phyllis still insists on setting up Michael with Sandy, while Stanley doesn't know anyone he hates that much to put on the card. Jim has an idea, but it's Pam's mom. She doesn't approve. Michael collects the cards and goes to the first name. Wendy, a hot and juicy redhead.

Reaction
Michael's optimistic until he realizes that he has called Wendy's restaurant. The lady on the phone obviously isn't Wendy, but he requests to speak to her. She explains it's a Wendy's restaurant, and Michael figures it out. That still doesn't stop him from ordering a Frosty and a baked potato. It was already ready, so it will be set aside until he gets there.

Originality
9 - Go Kevin! Not only does Mr. Malone save the day as far as the parking situation, but he pulls his first solo prank. His first attempt at getting at Michael was unsuccessful after assists from Pam and Ryan, but he pulls off this one flawlessly. He gets an extra point for the saucy redhead wording and a bonus point for taking no credit and staying silent about it.

Length Taken
9 - If Kevin would have called Wendy's to inform them of the situation and got someone over there in on it, that would have pushed things over the top. But, as it stands, a strong pranks all around.

Special Awards
The Fly on Your Own Award - Kevin goes all in for his first unassisted prank and slams it home.
The Simplicity Award - How much effort did that take, really? Write down Wendy...check. Make saucy redhead comment...check. Look up phone number for Wendy's...check. Hand to Michael Scott...check.
The Humble Pie Award - If not for Michael saying to "Wendy" that he is Kevin's friend, would we have ever known?

Pam, Ryan and Kevin Share their Grief

Episode
Grief Counseling (Season 3, Episode 4)

Pranker
Pam Beesly, Ryan Howard and Kevin Malone

Target
Michael Scott

Description
Michael has had his former boss, Ed Truck, die. He announces it to the office and Kelly wants to know if he’s ok. Sensing that he can get some attention, he invites anyone who wants, to console him in his office. After Creed lets Michael know about the nature of Ed’s death, he goes to Jan to look for answers. Continuing to sulk, everyone in the office looks to get Michael’s mind off the issue. Therefore, Michael calls a meeting in the conference room to get everyone’s feelings of death out in the open. Michael starts out and describes losing Ed. When Roy tries to get Pam out of the session, Michael (like the loving father of the family he is) waits until Pam gets back. Dwight gets the opportunity to express his feelings about the twin Dwight has “resorbed.” Stanley has the opportunity, but passes. Pam finally takes the reigns and explains about her aunt was the Hillary Swank character from Million Dollar Baby without letting Michael know. Ryan enthusiastically wants next as he describes the death of his cousin Mufasa, better known as The Lion King. Kevin begins to understand what is going on and he describes about how one “weekend” his uncle “Bernie” died.

Reaction
Michael catches on to what is transpiring after Kevin describes Bernie’s death. Michael misses on veiled references to Million Dollar Baby and The Lion King, but whenever someone makes mention of Weekend at Bernie’s, nothing gets past. Michael asks if this is some kind of game (Phyllis mentions the inclusion of a ball) and tries to start over. No one wants to continue and many go back to work. This causes Toby to mention a bird that died running into the company door. Michael freaks and wants a funeral for the bird.

Originality
7 – Pam gets high marks for thinking up a character to a movie that Michael definitely hasn’t seen. Ryan skirts the line of Michael’s tastes with a kids movie from the 90s and Kevin goes too far and mentions a film that is, without a doubt, somewhere at Michael’s condo on DVD. Pam and Ryan do a great job of not breaking when describing the death circumstances. As for Kevin, not so much.

Length Taken
6 – For a minute there, I thought Michael would fall for Kevin’s death reference and say something along the lines of, “Wow. That sounds just like Weekend at Bernie’s,” and the fun could continue. Pam and Ryan keep things going for as long as possible to stall for time, so an extra point for effort.

Special Award
Oh, So Close Award – Kevin’s reference was close to get Michael to believe it all and continue with the counseling. If not for a little giggling and too much emphasis on the words “weekend” and “Bernie,” it could have worked. At one point, you can even see Ryan realizing that Michael is going to figure out what is going on.