
Original Air Date: May 15, 2008
Well, it looks like H.R. man Toby really is leaving, after twelve years at Dunder Mifflin, and for Costa Rica, too. Despite the fact that he despises him, Michael wants to throw a big farewell party for Toby to celebrate having a huge weight lifted off his back. Obsessively frugal Angela is against a huge to-do due to a lack of funds, which leaves Phyllis in charge of finding an anti-gravity machine per Michael’s request after the boss hands over a shoeful of dough he’s saved.
Toby’s replacement, Holly (Academy Award nominee Amy Ryan, who was so good in Gone Baby Gone that I expected her to turn up looking haggard after a night of boozing and drugging), arrives and quickly manages to convince a downright rude Michael that she’s nothing like her predecessor by calling Toby boring to his face. She later reveals a charming ability to “get” Michael and his weird (for a grown businessman, at least) eccentricities, such as imitating Yoda.
It’s only a matter of time at this point before Michael falls hopelessly in love with the new woman in the office, and, sure enough, in the span of one commercial break, he’s already calling her Hollygram and making a mix tape for her commute into Scranton. Unfortunately, he forgets/doesn’t bother to inform Dwight that the hazing they agreed on before they met Holly is no longer necessary.
So, Dwight continues to feed her lies, including the claim that Kevin is slow in the brain. This inevitably leads to a love triangle of sorts because Holly is extra nice to allegedly mentally challenged Kevin, who predictably gets the idea that she’s totally into him because she wants him to bang her.

After he calls Jim in his office for advice on the mix tape, Michael’s declaration of his love for Holly leads Jim into a soliloquy about how people can find love at work, like he did with Pam. The discussion, along with the prior news that Pam was accepted at New York’s Pratt Institute and intends to go, then convinces Jim to propose to her at Toby’s goodbye party, and he gives Phyllis yet more money to by some fireworks for the occasion.
Jim’s also decides to take on Ryan, who he thinks is trying to push him out of his job. In response, he leaves a phone message that basically dares Ryan to force him out. I gotta say I love this new Jim who tries. There’s too many silly people who play games at work, so good on Jim for refusing to waste time on Ryan anymore. Watching a YouTube video of Ryan getting arrested for fraudulently double billing orders to mislead shareholders is an unexpected bonus that definitely trumps Oscar’s observation that the worst crime is the former intern’s beard.
Other highlights from the double episode include:
Toby’s painful exit interview, which Michael intended to use as a final torture-payback session when he thought he would be conducting it alone. Holly and Pam crash the meeting, however, and they get to see Michael’s literally sucky departure gift for Toby — a gift-wrapped rock with the note “Suck on this” attached.
Michael and Holly catch Meredith and Dwight, still unaware that Holly-hazing is no longer necessary, putting a raccoon in Holly’s car. Michael, at the height of his Holly infatuation, orders the hazing to stop with the announcement that Holly is the best thing to happen to Dunder Mifflin since World War II.
Kevin leaves Toby’s farewell party to pick up extra snacks and calls Michael, who’s busy bonding with likewise smitten Holly at the party, to hurry over. When Michael arrives, sneering Kevin is exiting the supermarket with very pregnant Jan. Worse, Michael’s not the daddy and, no, Jan didn’t cheat.
She went to a sperm bank because she’s not young anymore and instead of having enough breeding time to give Michael a shot, she felt the need to make her first and likely only child count. Later, Michael shocks (at least me) when he makes a choice between sex and kids — he thinks he can no longer have both — and concludes he’d rather be a father to Jan’s child than hook up with Holly (to Kevin’s massive delight).
Jim’s plan to propose to Pam at the party is hijacked by Andy’s proposal to tight-lipped Angela. Angela, clearly embarrassed and not interested, says okay simply because everybody’s looking at her.
Later, Phyllis catches her and Dwight — the two biggest prudes in the history of mankind — getting it on big time in the empty office. Meanwhile, Pam is *so* disappointed Jim didn’t propose while Toby is *so* excited he finally has a picture of just him and Pam.
Aside from establishing Amy Ryan’s Holly as someone to look forward to seeing again next season, the second part of “Goodbye Toby” is all about cliffhangers. As a result, the finale makes room for a number of logical, interesting developments when the series returns in the fall, such as Jim somehow getting Ryan’s job and moving to New York to be near Pam while she’s at Pratt. Speaking of which, let’s watch Ryan get arrested right now.
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[...] New York Magazine agrees with me that Oscar nominee Amy Ryan was the bomb on The Office’s fourth-season finale last Thursday. Sadly, the publication also reveals that although her character Holly is a permanent [...]