10 Worst Things Done by Characters in The Office

10. Pam Beesly: Self-Promoting via Fraud

After failing as a salesperson, Pam took advantage of the chaos following the Sabre takeover by simply claiming she had been promoted to "Office Administrator." She bluffed a spineless Gabe Lewis into signing off on the $41,500 salary by daring him to call her a liar to her face. It was a calculated act of workplace fraud that allowed her to create her own dream job out of thin air.

9. Andy Bernard: Abandoning the Office for Three Months

As manager, Andy took his family boat and sailed to the Bahamas for three months without telling his bosses or his girlfriend, Erin. He continued to collect his paycheck and expected his staff to cover for his total negligence. When he returned, he was incredibly entitled and showed zero appreciation for the people who had kept the branch afloat in his absence.

8. Phyllis Vance: Blackmailing Angela

After catching Angela and Dwight together, Phyllis spent weeks emotionally and professionally terrorizing Angela. She forced Angela to do all her menial chores and eventually demanded that Angela "confess" her affair during an office party. While Angela’s cheating was wrong, Phyllis’s sheer glee in using the information for psychological leverage showed a surprisingly vindictive side to her character.

7. Michael Scott: Framing Toby for D... Possession

Michael’s hatred for Toby Flenderson reached a criminal level when he purchased what he thought was high-grade marijuana (it was actually caprese salad) and hid it in Toby’s desk. He then called the police to report Toby. Michael was fully prepared to see an innocent man go to prison just because he found him "boring" and a "wet blanket" on office fun.

6. Angela Martin: Hiring a Hitman for Oscar

After discovering her husband (The Senator) was having an affair with Oscar, Angela didn’t turn to divorce court, she turned to a man named Trevor. She paid him to "take care of" Oscar, specifically requesting that he "break his knees" or worse. Though the hitman was incompetent and the plan failed, the fact that Angela was willing to commit a violent felony out of spite is a dark peak for her character.

5. Jim Halpert: The "Snowball Fight" Escalation

While Jim is often seen as the "sane" one, his psychological torment of Dwight during their snowball fight crossed into genuine cruelty. After Jim hit Dwight with a high-speed snowball in the office, Dwight retaliated with a complex psychological war. Jim eventually became so paranoid and aggressive that he pelted a Dwight-shaped snowman with a heavy umbrella, showing a side of Jim that was genuinely scary and out of control.

4. Michael Scott: Outing Oscar

After discovering Oscar was gay, Michael didn't just breach his privacy; he forced Oscar into a traumatic public outing in front of the entire conference room. To "prove" he wasn't homophobic, Michael then forced Oscar into a deeply uncomfortable and non-consensual kiss. This was a massive violation of workplace ethics and basic human decency.

3. Ryan Howard: The Fraud and Downward Spiral

Ryan went from a quiet "temp" to a corporate executive who intentionally misled Dunder Mifflin shareholders. He pushed a "Dunder Mifflin Infinity" website that he knew was failing and committed double-accounting fraud to inflate sales numbers. His arrogance and willingness to ruin the company for personal gain eventually led to his arrest in front of the entire staff.

2. Dwight Schrute: The Fire Drill

In an effort to "teach" the office about fire safety, Dwight staged a hyper-realistic drill that involved locking all the doors, cutting the phone lines, and heating door handles with a blowtorch. The chaos resulted in Stanley having a near-fatal heart attack. Dwight’s lack of remorse and his subsequent decision to cut the face off a CPR dummy made this one of his most unhinged and dangerous moments.

1. Michael Scott: Scott’s Tots

Widely considered the most "cringe-inducing" episode in television history, Michael’s ultimate sin was promising a class of third-graders that he would pay for their college tuitions. Ten years later, he had to face those students, now high school seniors, and admit he had no money. He essentially crushed the dreams of an entire classroom of underprivileged youth, offering them laptop batteries as a "consolation prize."