|Location:||Summer Glen, California|
|Death:||October 31, 1998|
|Portrayed By:||Adam Arkin|
|First Appearance:||Halloween H20: Twenty Years Later|
- "That's terrible. Take off your clothes. "
- ―Will Brennan.[src]
Will Brennan was the oldest of his siblings. When he was younger, his mother had an affair that his father had discovered when he came home early one night. Will's father beat up both the man she was having the affair with and his wife. They eventually patched things up but Will's father blamed Will for it as he felt Will let it happen and didn't tell him about it. This caused a rift between the two and also caused Will to have betrayal issues. As Will got older he became the guidance counselor at Hillcrest Academy. He was also the secret boyfriend of Keri Tate. They decided to have lunch that day where Keri told him that she thought she was losing her son John. She had also told him that she wanted to tell him her background at later time since he told her that he was a good listener and she figured she can trust him.
Will decided to say at Hillcrest while the students went off on their trip so he could keep watch over the students that didn't get to go on the trip. He checked up on Sarah Wainthrope and Molly Cartwell and told them if they needed anything to contact him or Miss Tate. Afterwards he had date with Keri where as soon as he arrived, they started to make out. In the middle of it, Keri told him that she wasn't who he thought she was and revealed that her name was actually Laurie Strode. She revealed more of her background to him and he slowly realized who her brother was. At first in disbelief, once he figured out that she was telling the truth, he told her that he most likely wouldn't come after her since it has been 20 years. Once he asks her how old she was, Laurie realizes that John is the same age as she was when Michael Myers attacked her.
Will watches in confusion as Laurie gets a gun and the phones are now dead. They decide to go towards the school where they find John and Molly getting attacked by Michael. They help John and Molly hide in a room while they try to find Michael. Laurie tries to save Will when she tells him to escape but he tells her that he isn't leaving without her and at that time, Will sees a shadow that looks similar to Myers, grabs Laurie's gun and shoots at the shadowy figure. It turns out to be the security guard Ronnie Jones. Upset that an innocent man was shot, they both don't notice Michael entering the same room as them. Laurie notices at the last second but it's too late for Will as Michael stabbed him in the back, lifted him in the air and then dropped him.