The Worst Thing Stanley Hudson Ever Did On The Office

For the paper salespeople of Scranton's Dunder Mifflin, their job certainly isn't the dream as they deal with the daily antics of regional manager Michael Scott (Steve Carell). While some characters on "The Office" find ways to break up the monotony, such as Jim Halpert (John Krasinski) regularly playing pranks on Dwight Schrute (Rainn Wilson), others find little joy in their employment.

Quite possibly the grouchiest of them all is Stanley Hudson (Leslie David Baker), a pessimistic salesman with a knack for sarcasm. Of course, Stanley has a few positive moments, such as his close friendship with co-worker Phyllis Vance (Phyllis Smith) and deep love for pretzel day. But for most of his run on "The Office," he never has a problem letting everyone know what he thinks — especially his boss.

In Season 4, Episode 16, when Michael insists that Stanley participate in a team meeting after he refuses several times, Stanley bluntly states, "Did I stutter?" This makes everyone, including Michael, incredibly uncomfortable.

However, this isn't the worst thing that Stanley does on "The Office." His most questionable act, which takes place outside the walls of Dunder Mifflin, is actually hurtful to a loved one.

In Season 6, Episode 1 ("The Gossip"), Michael is desperate to be included in the rumors circling around the office. When an intern lets slip that he spotted Stanley at the club dancing with and kissing a woman, Michael assumes it was Stanley's wife, Teri (Joanne Carlsen), and gets excited to spill how his employee is having a midlife crisis. But when Phyllis reveals that Teri is out of town at an interior decorating expo, and that "Stanley hates crowds, kids, and music," Michael and the intern realize the woman wasn't Teri.

Many false rumors are started in this episode — courtesy of Michael — but Stanley's affair with his nurse, Cynthia (Algerita Wynn), proves to be fact. Though he was allegedly meeting Cynthia to break it off with her, this doesn't undo the fact that he was unfaithful to Teri behind her back.

It also doesn't seem like Stanley feels too bad about his actions. On the contrary, he has a blasé attitude when it comes to extramarital affairs. In a later episode, while several Dunder Mifflin workers are away on a business trip in Florida, Jim can't get rid of Cathy Simms (Lindsey Broad), his wife Pam Beesly's (Jenna Fischer) temporary replacement during her maternity leave. Cathy is attracted to Jim and adamantly tries to seduce him by showing up at his hotel room. When Stanley sees Cathy in Jim's bed, he tells him, "Be careful, Jim, it gets easier and easier."

This begs the question, how many affairs has Stanley actually had? He's by no means the only character on "The Office" to have done so — Angela's (Angela Kinsey) multi-season affair with Dwight comes to mind, for a start — but considering how far he's usually removed from the most harmful drama, Stanley's affair with Cynthia is by far his worst action on the show.