‘The Office’ stars unpack Toby’s departure and Holly’s arrival in the ‘Goodbye, Toby’ episode

Goodbye, Toby. Hello, Holly.

That’s the main gist of the Season 4 finale of The Office, “Goodbye, Toby,” which was so jam-packed with delightful storylines that it became a rare two-part episode.

On the latest episode of the , Office stars Jenna Fischer and Angela Kinsey chatted all about the first part of “Goodbye, Toby,” which was written by Jen Celotta and Paul Lieberstein and directed by Paul Feig. 

For those who need a refresher, “Goodbye, Toby” follows the Dunder Mifflin crew on one of the best days of Michael Scott’s life. His arch rival Toby is finally living out his dream of moving to Costa Rica, and Phyllis is tasked with throwing a big celebration in the parking lot. A new HR rep, Holly Flax (Amy Ryan) also arrives for her first day of work, and as fans know, Michael becomes absolutely smitten with her.

This particular episode of the podcast only focuses on the Part 1 of “Goodbye, Toby,” but Fischer and Kinsey revealed some delightful behind-the-scenes tidbits about writing, filming, and casting the show. Here are three standout revelations:

1. Why Toby said goodbye in the first place

As we noted earlier, Paul Lieberstein — a writer on the show who also played Toby Flenderson — co-wrote Toby’s goodbye episode. Why? Well, he was about to take over as co-show runner and needed to focus solely on writing for a while.

“I find it very funny that Paul had to write himself out of the show,” Fischer mused.

“I thought it was funny, too. But knowing Paul, because he’s very practical, it was probably like, ‘Well, it needs to be done,'” Kinsey added.

Fischer went on to explain that Lieberstein and Celotta took over as show runners in Season 5, because Greg Daniels went to work on Parks and Recreation.  

To get the full scoop on Toby’s goodbye episode, Fischer reached out to Lieberstein who sent a voice memo explanation. 

“Jen Celotta and I were taking over as show runners for Season 5, and that was absolutely part of getting rid of me,” he explained. “Did we know for a fact I’d be coming back? No, not for a fact. Didn’t really think about it that far in.”

2. The finale was so much bigger than fans knew

The “Goodbye, Toby” that fans saw was a delightful two-part episode. But before cuts, the original script — which Celotta and Lieberstein wrote in just five days — was a whopping 75 pages.

“There [were] a lot of things [that] started,” Lieberstein said when discussing the many storylines in the finale. “Pam’s acceptance to art school — that was something we had talked about for a long time. I always knew she liked it, but we were looking for a whole new complication after doing so much with the romance. And then Angela’s engagement to Andy. We always knew that was not a relationship to be. That was a bad relationship, a comedy relationship. But it was fun stuff, obviously.”  

Fischer also chatted with Celotta, who explained the writing process in more detail.

“[Celotta] said they had an outline and they divided up the work. They each wrote different parts and then they put it all together and did a rewrite together. So, I mean, I guess there were two people on it. But still,” Fischer shared. “Also the original cut of this episode came in at seventy two minutes and they had to cut it down to 40 minutes.”

Kinsey, who found her original “Goodbye, Toby” script, explained that there were so many scenes that didn’t make it into the episode. And though there are some wonderful deleted scenes from the two-parter, there were even more scenes filmed that didn’t make the deleted scenes cut. 

3. How Amy Ryan became the perfect Holly Flax

Michael not only says goodbye to Toby in this episode, but he also meets his future love interest, Holly Flax. 

I’m sure tolerating, let along falling for, Toby’s replacement never crossed Michael’s mind, but Amy Ryan’s portrayal of Holly was impossible not to love, so he didn’t stand a chance. In fact, Ryan was so perfect for the part that she didn’t even have to audition.

“Amy did not have to audition for the role of Holly Flax. It was offered to her,” Fischer explained. “This is why: First of all, Amy Ryan had just been nominated for an Academy Award… She’d been nominated for a movie called Gone Baby Gone. And in addition to that, the writing staff of The Office was slightly obsessed with the TV show The Wire, and Amy had been on The Wire. And whenever we had, like, big guest star roles come up, the writers would try to get cast members from The Wire to do them. I mean, spoiler alert: Idris Elba is coming up.”

Fischer revealed that the story of Ryan being cast as Holly runs even deeper, and Paul Lieberstein shared the details.

“[Amy’s] agents were asking her, ‘Well, what do you want to do?’ And she said, ‘I want to do The Office.’ And at the very same time, we were talking about her,” Lieberstein said. “I don’t really know who reached out to who first. I worked with Amy like a million years ago on another show. And we knew each other. And I was I was all for it. I loved working with her both times.”

Lieberstein explained that they didn’t know how much of an arc they were going to give Ryan at first, but as fans know, Michael and Holly became endgame.

“[Amy’s] agents were asking her, ‘Well, what do you want to do?’ And she said, ‘I want to do The Office.'”

“We wanted to kind of test it out and see cause you never know about chemistry, right? You never know if she’s going to have chemistry with Steve. And she sure did,” Lieberstein said. “I don’t think we knew that this was going to be the love of his life. We hadn’t planned it that far ahead. We were also watching what happened and reacting to it.” 

So there you have it folks, Amy Ryan was such a big fan of The Office that she pursued a role on the show. They originally booked her for a six-episode guest role in Season 5, but she kept returning because Holly and Michael’s chemistry was such a hit.

Be sure to listen to the full podcast episode for more behind-the-scenes stories from filming “Goodbye, Toby.”

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