Meredith Palmer (Kate Flannery) - "Moroccan Christmas" (Season 5). The Office drunk gets to go first. And there are so many moments that made us all laugh our asses off. When she got hit by Michael's car, bit by a bat, when she ate Angela's hand sanitizer to get drunk. However, "Moroccan Christmas" is her standout episode. when she sets her hair on fire while dancing drunk and Michael then tries to start an alcohol intervention. He dupes her by saying he will take her to a bar, and when she realizes he's taking her to rehab, she tries to escape.
Angela Martin (Angela Kinsey) - "Christmas Party" (Season 2). Another Christmas episode, which The Office always did so well. Angela is the head of the party planning committee, and her Christmas party is ruined throughout this episode. Michael first ruins everyone's party by playing "Yankee Swap". He then makes it right by buying a ton of alcohol for everyone. Although everyone else has a satisfying end to the party, Angela's ends with her out back by the dumpsters throwing, then smashing, various Christmas ornaments.
Michael Scott (Steve Carell) - "The Injury" (Season 2). It's hard to pick one for the star of the show, but "The Injury", when he accidentally burns his foot on a George Foreman grill in bed, is an abosolute highlight. It allows Michael to shine in a ridiculous way as he plays up his burnt foot and the lack of care he gets from everyone else in the office, calling it a "disability".
Pam Beesly-Halpert (Jenna Fischer) - "The Dundies" (Season 2). I'm leaving out the Jim & Pam combo moments ("Casino Night", "Booze Cruise", "Niagara", "A.A.R.M"). So my favorite moment where Pam shines alone was when she drank way too much at The Dundies. In just one night, she falls off a chair, wins the "Whitest Sneakers" dundie, kisses Jim, screams "BEST DUNDIES EVER!" and gets banned from Chili's.
Jim Halpert (John Krasinski) - "Pilot" (Season 1). I'm giving Jim the pilot episode, since it introduced us to his first ever prank of Dwight, which is a running stoyline we've looked forward too for the entire run of the series. It all started here, with Dwight's stapler being put into Jell-O, thus creating a prank copied by fans of the show.
Dwight Schrute (Rainn Wilson) - "Livin' the Dream" (Season 9). Dwight finally has two of his dreams come true. He receives a black belt he doesn't really deserve, then he finally becomes the manager of Dunder Mifflin Scranton, which he totally deserves. It was a satisfying moment for fans to see Dwight finally become manager.
Phyllis Lapin-Vance (Phyllis Smith) - "Phyllis' Wedding" (Season 3). Phyllis and Bob Vance, Vance Refrigeration finally get married. The funny part is Phyllis steals all of Pam's ideas from her abandoned wedding to Roy. She also allows Michael to push her father's wheelchair down the aisle so she can get six weeks vacation for her honeymoon.
Stanley Hudson (Leslie David Baker) - "Initiation" (Season 3). Pretzel Day. That's all that really needs to be said. Its Stanley's favorite day of the year, and he actually gets along with Michael as they both wait in line for their free pretzel.
Kelly Kapoor (Mindy Kaling) - "Lecture Circuit" (Season 5). Kelly tells off Jim & Dwight for forgetting her birthday, which leads to Jim & Dwight having to team up to make up for it by throwing Kelly a party, as she dictates what they can do. We also find out Kelly was in juvy when she was 14 for stealing her ex-boyfriends boat.
Ryan Howard (BJ Novak) - "Night Out" (Season 4). Ryan is oddly friendly during the start of this episode when he returns to Scranton to unveil the "Dunder Mifflin Infinity 2" website, after the first one was overrun by sexual predators. Michael & Dwight go to New York to see him because they want to party, and we learn Ryan is on drugs.
Kevin Malone (Brian Baumgartner) - "Costume Contest" (Season 7). In this Halloween episode, we get to see Kevin dressed as both Phyllis and Michael Moore. He also has beef with the new salesman Danny because he dumped Pam years ago. He decides not to go to the bar with Danny to be loyal to Jim & Pam. I always loved the moments when the cast would show their loyalty for one another.
Erin Hannon (Ellie Kemper) - "Classy Christmas" (Season 7). Erin finally meets Holly for the first time after hearing about her from Michael. Throughout the episode though, she tells the cameras that she doesn't understand what Michael sees in Holly, wondering why people think she is attractive. When Holly hurts Michael's feeling for having a boyfriend, Erin gives her the cold shoulder.
Oscar Martinez (Oscar Nunez) - "Business Trip" (Season 5). Oscar travels on a sales call to Canada with Michael & Andy. He gets drunk and lets loose in a way we weren't used to seeing, getting Andy to drunk dial Angela.
Creed Bratton (Creed Bratton) - "Product Recall" (Season 3). An obscene watermark of a "beloved cartoon duck & mouse" goes out, all thanks to Creed. He saves his job by framing someone at the paper mill. He gets a card for the fired worker and collects money from everyone in the office, which he then pockets for himself. Creed was always good for these quick hitting moments, and this episode was full of them.
Darryl Philbin (Craig Robinson) - "The Negotiation" (Season 3). While seeking a raise, he finds out that Michael barely makes more than him and decides to "help" Michael get more money. While he ultimately does get Michael more money, he can't help but play tricks on him by teaching him fake "black man slang" and making fun of him for wearing a suit made for women.
Andy Bernard (Ed Helms) - "Secret Santa" (Season 6). Andy expertly shows his reputation as the shows most annoying character when he requests Erin for secret Santa, getting her the entire 12 Days of Christmas, with some of the birds injuring her.
Jan Levenson (Melora Hardin) - "Dinner Party" (Season 4). Watching Jan & Michael having a party in their small condo as their frustration for one another keeps getting worse throughout the episode is a thing of comedic beauty. We get to hear the song "Just One Night" by her young former assistant Hunter, who she still has a thing for.
Holly Flax (Amy Ryan) - "Goodbye, Toby" (Season 4). Our first meeting with Holly doesn't go so well for her. As the new HR rep, Michael instantly dislikes her in the beginning. He tells her that Kevin is mentally challenged, making her interactions with Kevin throughout the episode hilariously entertaining. It causes him to think she is attracted to him when she gives him this special treatment.
Toby Flenderson (Paul Lieberstein) - "Goodbye, Michael" (Season 8). Michael says bye to Toby and doesn't make fun of him for the first time ever. Just when you think he might miss Toby, Michael quickly gets annoyed when he finds out Toby has a brother in Boulder, Colorado where he is moving. We later see Toby skype with him, and he is exactly the same boring guy as Toby.
Angela Martin (Angela Kinsey) - "Christmas Party" (Season 2). Another Christmas episode, which The Office always did so well. Angela is the head of the party planning committee, and her Christmas party is ruined throughout this episode. Michael first ruins everyone's party by playing "Yankee Swap". He then makes it right by buying a ton of alcohol for everyone. Although everyone else has a satisfying end to the party, Angela's ends with her out back by the dumpsters throwing, then smashing, various Christmas ornaments.
Michael Scott (Steve Carell) - "The Injury" (Season 2). It's hard to pick one for the star of the show, but "The Injury", when he accidentally burns his foot on a George Foreman grill in bed, is an abosolute highlight. It allows Michael to shine in a ridiculous way as he plays up his burnt foot and the lack of care he gets from everyone else in the office, calling it a "disability".
Pam Beesly-Halpert (Jenna Fischer) - "The Dundies" (Season 2). I'm leaving out the Jim & Pam combo moments ("Casino Night", "Booze Cruise", "Niagara", "A.A.R.M"). So my favorite moment where Pam shines alone was when she drank way too much at The Dundies. In just one night, she falls off a chair, wins the "Whitest Sneakers" dundie, kisses Jim, screams "BEST DUNDIES EVER!" and gets banned from Chili's.
Jim Halpert (John Krasinski) - "Pilot" (Season 1). I'm giving Jim the pilot episode, since it introduced us to his first ever prank of Dwight, which is a running stoyline we've looked forward too for the entire run of the series. It all started here, with Dwight's stapler being put into Jell-O, thus creating a prank copied by fans of the show.
Dwight Schrute (Rainn Wilson) - "Livin' the Dream" (Season 9). Dwight finally has two of his dreams come true. He receives a black belt he doesn't really deserve, then he finally becomes the manager of Dunder Mifflin Scranton, which he totally deserves. It was a satisfying moment for fans to see Dwight finally become manager.
Phyllis Lapin-Vance (Phyllis Smith) - "Phyllis' Wedding" (Season 3). Phyllis and Bob Vance, Vance Refrigeration finally get married. The funny part is Phyllis steals all of Pam's ideas from her abandoned wedding to Roy. She also allows Michael to push her father's wheelchair down the aisle so she can get six weeks vacation for her honeymoon.
Stanley Hudson (Leslie David Baker) - "Initiation" (Season 3). Pretzel Day. That's all that really needs to be said. Its Stanley's favorite day of the year, and he actually gets along with Michael as they both wait in line for their free pretzel.
Kelly Kapoor (Mindy Kaling) - "Lecture Circuit" (Season 5). Kelly tells off Jim & Dwight for forgetting her birthday, which leads to Jim & Dwight having to team up to make up for it by throwing Kelly a party, as she dictates what they can do. We also find out Kelly was in juvy when she was 14 for stealing her ex-boyfriends boat.
Ryan Howard (BJ Novak) - "Night Out" (Season 4). Ryan is oddly friendly during the start of this episode when he returns to Scranton to unveil the "Dunder Mifflin Infinity 2" website, after the first one was overrun by sexual predators. Michael & Dwight go to New York to see him because they want to party, and we learn Ryan is on drugs.
Kevin Malone (Brian Baumgartner) - "Costume Contest" (Season 7). In this Halloween episode, we get to see Kevin dressed as both Phyllis and Michael Moore. He also has beef with the new salesman Danny because he dumped Pam years ago. He decides not to go to the bar with Danny to be loyal to Jim & Pam. I always loved the moments when the cast would show their loyalty for one another.
Erin Hannon (Ellie Kemper) - "Classy Christmas" (Season 7). Erin finally meets Holly for the first time after hearing about her from Michael. Throughout the episode though, she tells the cameras that she doesn't understand what Michael sees in Holly, wondering why people think she is attractive. When Holly hurts Michael's feeling for having a boyfriend, Erin gives her the cold shoulder.
Oscar Martinez (Oscar Nunez) - "Business Trip" (Season 5). Oscar travels on a sales call to Canada with Michael & Andy. He gets drunk and lets loose in a way we weren't used to seeing, getting Andy to drunk dial Angela.
Creed Bratton (Creed Bratton) - "Product Recall" (Season 3). An obscene watermark of a "beloved cartoon duck & mouse" goes out, all thanks to Creed. He saves his job by framing someone at the paper mill. He gets a card for the fired worker and collects money from everyone in the office, which he then pockets for himself. Creed was always good for these quick hitting moments, and this episode was full of them.
Darryl Philbin (Craig Robinson) - "The Negotiation" (Season 3). While seeking a raise, he finds out that Michael barely makes more than him and decides to "help" Michael get more money. While he ultimately does get Michael more money, he can't help but play tricks on him by teaching him fake "black man slang" and making fun of him for wearing a suit made for women.
Andy Bernard (Ed Helms) - "Secret Santa" (Season 6). Andy expertly shows his reputation as the shows most annoying character when he requests Erin for secret Santa, getting her the entire 12 Days of Christmas, with some of the birds injuring her.
Jan Levenson (Melora Hardin) - "Dinner Party" (Season 4). Watching Jan & Michael having a party in their small condo as their frustration for one another keeps getting worse throughout the episode is a thing of comedic beauty. We get to hear the song "Just One Night" by her young former assistant Hunter, who she still has a thing for.
Holly Flax (Amy Ryan) - "Goodbye, Toby" (Season 4). Our first meeting with Holly doesn't go so well for her. As the new HR rep, Michael instantly dislikes her in the beginning. He tells her that Kevin is mentally challenged, making her interactions with Kevin throughout the episode hilariously entertaining. It causes him to think she is attracted to him when she gives him this special treatment.
Toby Flenderson (Paul Lieberstein) - "Goodbye, Michael" (Season 8). Michael says bye to Toby and doesn't make fun of him for the first time ever. Just when you think he might miss Toby, Michael quickly gets annoyed when he finds out Toby has a brother in Boulder, Colorado where he is moving. We later see Toby skype with him, and he is exactly the same boring guy as Toby.
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