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By Shaun Flagg   |  The Office  |  March 02, 2009


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With “The Office” airing the second of consecutive reruns this week, I thought this might be a good time to take a look back and relive some of the best episodes of the first five seasons.

I originally planned on putting together a Top 10 list, ala Letterman, but struggling to cut my list down, I decided to take the chicken’s way out and pick out my three favorite episodes from each season.

After reading my picks, feel free to mock, ridicule and criticize my thought process. In other words, do what you all usually do …

Season One

“Pilot” — A great episode? No. But a solid table-setter. Since I had watched the BBC America version of the show, I had an idea of what to expect, but because BBC shows haven’t exactly translated into American success (“Coupling” anyone?) my expectations weren’t high. This debut easily exceeded them.

“Basketball” — By far my favorite episode of the abbreviated first season with trash-talking Michael showing he absolutely, positively has no game. After talking Stanley into playing on his team, Michael is mortified to see his “ringer” is more Michael Jackson than Michael Jordan. Nice capper to the episode with Kevin nailing jumper after jumper.

“Diversity Day” — Dunder Mifflin corporate orders diversity training for the Scranton branch in reaction to Michael’s bleep-filled Chris Rock imitation. The best scene features staff members placing a card on their foreheads and then having to figure out their ethnicity through how they are treated. A surprisingly straight-laced Kelly slaps Michael after his racist, convenience store crack.

Season Two

“Dundees” — This blatant advertisement for Chili’s includes a rapping Michael and a toasted Pam. Handing out awards to all his workers, Michael shows his true feelings by giving Ryan the “Hottest in the Office” award. Pam is ecstatic over receiving the “Whitest Sneakers” award and celebrates by kissing Jim.

“Christmas Party” — A simple Secret Santa celebration devolves into a selfish free-for-all — AKA “Yankee Swap” — with everyone hoping to get the iPod Michael had bought for Ryan. Episode ends with a drunken Meredith (sorry, redundant) stripping naked for Michael, who, of course, snaps a picture and leaves.

“Casino Night” — Michael sets up a night of gambling and drinking — all to benefit charity in this stellar season finale. Michael juggles Jan and Carole his Realtor. Cardsharp Kevin is annoyed after losing to Phyllis. Jim confesses his love to Pam for the first time and she says she doesn’t share his feelings, only to kiss him later.

Season Three

“Cocktails” — Michael, Dwight, Jan, Jim and Pam attend a party at the home of David, the Dunder Mifflin CFO. While Dwight spends his time doing an all-too-thorough home inspection, Michael and Jan come out as a couple. Meanwhile, office workers go to a local bar where Toby spends his entire night trying to win a stuffed animal for Pam. He then gives it to her and she suggests he give it to his daughter. Pam admits to Roy that she kissed Jim, giving Roy and his brother an excuse to trash the place.

“Beach Day” — Michael takes his staff to a local lake for some bonding time, “Survivor” style. Andy, wearing a sumo outfit, tragically, is lost at sea. Pam walks across burning coals and tells Jim he is the reason why she called off her wedding.

“The Job” — With several office workers vying for a regional manager job, Michael is distracted by his relationship with Jan. He plans on breaking up with her until she brings out the big … Well, let’s say she wins him back. In a nice twist, Ryan gets the promotion and takes joy in telling Kelly to take a hike.

Season four

“Dinner Party” — This just might be my favorite episode, with Michael and Jan hosting a stress-filled party during which they fake fondness — “Babe” — while resisting the urge to break each other’s things, including Michael’s sweet $200 plasma TV. Jim is so desperate to leave that he lies that his apartment has been flooded and is willing to sacrifice Pam, who will not let him escape.

“Night out” — Another classic in which Michael and Dwight go to New York to join Ryan, who has developed some unfortunate habits since leaving Scranton. Back at the office, the staff works late and is locked in. Toby accidentally makes his feelings for Pam known to everyone. Mortified, he announces he’s leaving for Costa Rica and jumps the security fence. Episode ends with Ryan admitting he has a problem while Michael calls it one of his favorite nights ever.

“Goodbye Toby” — Another excellent season finale with the staff — including a giddy Michael — saying goodbye to the head of HR. Michael immediately is smitten with Toby’s replacement, Holly. My favorite scenes are between Holly and Kevin, who she thinks is, um, “special,” while he thinks she’s flirting. Michael learns Jan is pregnant — but not by him — and Andy beats Jim to the proposal punch by asking Angela to marry him. Angela celebrates her engagement with a rendezvous with Dwight and the couple are caught by Phyllis.

Season five

“Business Trip” — Michael, Andy and Oscar go to Winnipeg for a business trip where Oscar talks Andy into drunk-dialing Angela. The look on Andy’s face the next day when Oscar tells him it wasn’t a dream, that he really had called Angela the night before, is priceless. Back at the office, Ryan tells Kelly to drop Darryl, which she does, in a text message and Darryl messages back “it’s cool.” Ryan realizes, to his horror, he is stuck with Kelly again, which is reminiscent of his realization of the mistake he had made when he originally hooked up with her — on April 13.

“The Duel” — After Andy learns of Angela’s affair with Dwight, the men face off, only to realize, heck, she’s not worth it.

“Stress Relief” — The post-Super Bowl episode was stretched a little thin to last the full hour, but the opening with Dwight teaching the staff a lesson on fire safety — complete with cats falling through ceilings and Stanley suffering a heart attack — probably is the show’s most inspired scene ever.

OK, so that’s my far-from-scientific Top 15. Let me know what you think. What picks do you agree with (if any)? What episodes shouldn’t I have included? What episodes was I a moron for not including?

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