Chuck Octagon

Chuck Octagon is a news reporter in the Greater Boston area. He is voiced by Jeff Van Dreason.

Reporting on Red Line
Chuck worked as an on-the-street reporter for 7 News. He interviewed Mallory several times as a key witness, and asked for citizens' opinions on Red Line both before and after the referendum.

When Chuck met Melissa Weatherby by chance, she agreed to arrange an interview between him and Charlotte Linzer-Coolidge. Chuck asked potentially harsh questions, criticizing Red Line's jail in Dorchester and the disappearance of The Mayor of the Red Line. He quickly admitted that he has to ask those questions because of his boss and didn't want to upset Charlotte.

Chuck continued to report on Red Line. At one point, he interviewed Mallory and learned that The Lottery nearly had a second molasses-related attack not long after the first.

Wedding
Chuck became engaged to Andy Wood, one of his coworkers. His boss suggested that they hold the wedding on Red Line. Chuck met with Charlotte to ask her to refuse, and told her that if she couldn't do so, he would release information about the second molasses attack. However, not long afterwards, Dipshit Poletti blackmailed Chuck into holding his wedding in Red Line after all. Chuck angrily agreed.

He interviewed Charlotte, along with Isabelle Powell and Emily Bespin, for News 7's election profiles. In the process, he announced that he would be holding his wedding as a live TV special in Red Line. He made a point of asking Charlotte about her father leaving her as a child. Charlotte, Isabelle, and Emily all cut off his lines of questioning to make their own points.

Chuck met with Charlotte to discuss his wedding. He had exacting plans, including a live dove release from a custom-built car with a canopy. He accused Charlotte of blackmailing him, which she was too shocked to deny. He continued planning for his wedding, and asked Mallory to be his designated witness.

Chuck ultimately married Andy in Red Line, in a disastrous wedding. The Lottery attacked and spewed scalding hot baked beans into the train car. Charlotte pulled Chuck and Andy under cover, but Mallory was badly burned. He visited her afterwards, but she refused to talk about her injuries. Chuck and Andy honeymooned together in Barcelona.

Afterwards, Chuck returned to report on ThirdSight Media.

Behind the scenes

 * Chuck is voiced by show co-creator Jeff Van Dreason, who conducts the candid interviews that appear in the show. Beginning in The Watcher Over ThirdSight, the transcripts list Chuck as the interviewer rather than Jeff.
 * Chuck's in-canon interviews with Mallory in Leon at the Watch Factory and Leaps of Faith are credited to Jeff, not Chuck.

Season One

 * Leon at the Watch Factory (unofficial)
 * Leaps of Faith (unofficial)
 * Vox Populi

Season 1.5

 * How Was Your Commute?

Season Two

 * Mayor Linzer-Coolidge and the Lottery
 * Extinction Event at the Olive Garden
 * The Red Line Tea Party
 * Breaking Kayfabe
 * Profiles with Chuck Octagon, Election Special
 * Liars and Legerdemain
 * Chuck Octagon’s News Seven Wedding Special, Live from Red Line, with Special Guest Andy Wood
 * On the Advice of Mary Wollstonecraft

Season 2.5

 * Shine a Light on ThirdSight