All-Time Faves is a new feature I'll be doing on occasion where I talk about some of my favourite episodes of television and what makes them special. To kick it off we'll be looking at my all-time favourite episode of my all-time favourite show: Booze Cruise, the 11th episode of the 2nd season of The Office, which originally aired January 5th 2006.
"Never, ever, ever give up"
There are many episodes of The Office that serve as good entry points for the show for someone who has never seen an episode. The Pilot is a pale imitation of the British originals pilot and nowhere close to what the show would become but it introduces the main characters well enough and if you haven't seen the British version, it plays better. The season 2 premiere, The Dundies is a better entry point. The writers have figured out the tone that works best for writing Michael and for the show, and it's packed full of great little jokes and character beats plus the first "kiss" for Jim and Pam. My first episode back in the day was the episode that follows this one, The Injury. It's hands-down one of the funniest episodes the show ever did and it gave me a good sense of what the characters and comedy of the show were like, instantly making me want to see more. However if you were to ask me what episode of The Office to start with, I would point you to Booze Cruise each and every time.
Written by Greg Daniels who developed the show for American Television, and directed by Ken Kwapis who directed several crucial installments of the show, including both the first and last episodes, and Casino Night, Booze Cruise is my absolute favourite episode of The Office. It features an incredibly funny first half with classic joke after classic joke before seamlessly seguing into a second half that's heartbreaking and introspective, but still hilarious, a perfect blend of everything The Office was so good at in its prime. It has not one but two of the very best scenes the show ever did. It's a key turning point in the Jim/Pam relationship, but also a turning point in the Jim/Michael relationship. Also, unlike some of the other best episodes of the show, it requires no previous knowledge of The Office to be impactful, which is why I recommend it as a starting point. Casino Night (my second-favourite episode) is incredible television and arguably better than Booze Cruise, but it's also the culmination of the season that preceded it, full of callbacks and pay-offs to character relationships that are going to mean nothing to you if you haven't seen at least part of the season up to this point, particularly Booze Cruise, which sets up the emotional through line for the back half of the season. By the end of Booze Cruise, you have a good idea of who Michael, Jim, Pam, and Dwight are, a good grasp of the actual office dynamics, a clear understanding of Jim's feelings towards Pam, and most crucially a reason to believe in their love story beyond "the show wants us to".
The trick Booze Cruise pulls though is that if you were to go into it having heard nothing about it, you'd have no idea how important it was. The first half is standard Office, largely focused on Michael's antics with the rest of the Dunder Mifflin team reluctantly along for the ride. This time, Michael has planned a top secret "first quarter camaraderie event", which turns out to be a January booze cruise (When it's cheaper) along Lake Wallenpaupack. It's not just another party though. Michael has also planned what he hopes will be an inspirational presentation on leadership (which is entirely based on the word ship being part of the word leadership as it's "derivation"). That desire to be an inspiring boss who is going to turn lives around with what he has to say is what becomes Michael's motivation for the episode and what keeps his antics from feeling too grating. Michael's intentions to inspire though bump up with the intentions of Captain Jack, the ship's captain and "party captain" who takes both of his jobs very seriously. Portrayed by Rob Riggle in one of his best performances, Captain Jack is one of the best one-time guest characters The Office ever had, a reasonable guy with the right amount of "loudmouth alpha dog" typically found in a Rob Riggle character who just wants to do his job and have a good time, and who becomes increasingly firm on shutting down Michael's presentation when it interferes with his schedule. He's given enough personality to feel like more of a character than the plot device he could've been reduced to and that makes his pseudo-power struggle with Michael all the funnier and an episode solely based on that power struggle would still have been one of the better episodes of The Office. Just when you think you know where the episode is going however, Pam steps away from her fiance and the snorkel shot crowd for a minute to talk to Jim.
The best 30 seconds The Office ever did contains no jokes and barely any dialogue. It's so strong I had forgotten it happens at the episode's mid-point instead of near the end. It starts when Pam jokingly asks Jim what it's like to date a cheerleader. Jim chuckles and starts to answer but then just doesn't. He simply stares at Pam as if he wants to tell her what he really wants while she waits for him to say something, anything. For 27 whole seconds neither of them say nothing at all, but those 27 seconds tell us everything. Greg Daniels has said as he watched the scene in the edit bay he was yelling for Jim to kiss Pam and you can't blame him. The episode has stealthily reminded us that Pam's engagement has no end in sight and that Roy just isn't a good fit for her. You get the sense that if Jim were to kiss Pam then that would be it and Pam would break it off with Roy while Jim broke it off with Katie and they would get together at last. Except Jim isn't ready to let Pam know what has been clear from the start so he doesn't kiss her because he can't do it now. He just can't. So Pam breaks the silence, makes an excuse and leaves. The moment has passed. It's a beautiful sequence from beginning to end with some of the best acting John Krasinski and Jenna Fischer ever did, but it's also a lot more than that.
It was always easy to root for Jim and Pam. Krasinski and Fischer had terrific chemistry from the beginning and the source material of the British original gave it a real and relatable hook: the struggles of being in love with someone who loves someone else. The best Will They/Won't They romances need a big obstacle to make the question an actual question and Pam's engagement was a big one. The thing is, as easy as it was to root for Jim and Pam, it was easy to get the sense that you just wanted them to get together because that's how shows like this works and that's what The Office wanted you to do. The attractive people with strong chemistry get together because why not? Yeah you were invested, but you had to be invested. What makes the 27 seconds of silence on Booze Cruise so powerful is that it sells you on the idea of a powerful emotional bond between Jim and Pam that transcends television conventions and writing. You believe Jim is in love with this girl not because he's the romantic lead of a television sitcom, but because he deeply, truly loves her and when you believe that, you believe in love. Suddenly rooting for Jim and Pam isn't an obligation but something you actually truly want to see in your heart of hearts. And that honest investment is crucial to the success of the back half of the season, which I know from experience. When I originally watched the 2nd season of The Office, it was on DVDs I rented one disc at a time from the video store that I viewed in the odd order of discs 3-4-1-2. So Booze Cruise was actually the last episode of the second season that I watched, and once I rewatched the second half of the season (which I believe I did immediately), all the Jim/Pam moments that I liked before became that much more powerful. The Casino Night confession, rejection, and kiss became that much more powerful because it actually felt like it meant something. Those 27 seconds are some of the most meaningful seconds The Office ever did and they become amplified by the heartbreak that happens next.
Up to this point, Pam's engagement had been nothing but a plot device, a contrivance to keep Pam unavailable and Jim pining, letting the pair have sweet moments while also giving them a good reason to never do anything about their feelings. It was a reliable story engine but there was no stakes to it, no investment in the idea of Pam actually marrying Roy beyond occasional lip service to the idea and no reason to assume that this would change anytime soon. Even after those 27 seconds, shortly followed by Jim's private assertion to the camera (and to us viewers) that if the office was on fire he would save the receptionist (the closest he's ever come to verbalizing his feelings), it feels like we're about to go back to business as usual. So when a very drunk Roy is inspired by Captain Jack's story of marrying his first wife the day after he got back from Desert Storm and finally decides to set a date for the wedding, it's a bigger shock than it should be. Suddenly Pam's engagement isn't something that can easily be cast off, but a very real thing that feels urgent and can't be ignored anymore. We had a reason to believe in Jim and Pam's love and now suddenly we don't. That moment between them happened two minutes earlier but now it feels like an eternity ago. Tellingly, Jim and Pam don't interact for the remainder of the episode and Pam doesn't even look at him, caught up in the rekindled passion of her engagement. Jim doesn't say much but just like before, his face tells us everything. This is the worst night of his life.
If Booze Cruise has a false note it's the episode's treatment of Jim's girlfriend Katie, who is played by Amy Adams of all people. Katie was introduced in the season 1 finale Hot Girl as pretty much that, a hot girl for Jim to date so we knew he had a love life outside of pining for Pam. She was never going to stick around the show for long (Adams was weeks way from her first-ever Oscar nomination for Junebug when this aired) so the show never bothered to define her or make her more than "Jim's temporary girlfriend". It's not the worst thing in the world, but Adams brought so much personality and life to what little she was given that it feels like a waste when a heartbroken Jim callously breaks up with her. Hindsight also definitely plays a part in why the Katie break-up feels so off. The Office definitely wasn't the first or the last show to have a disposable love interest, but the fact that Amy Adams became such a high-profile actress winds up drawing a lot more attention to how superfluous Katie is than it would with someone lesser-known in the role. It's a small blip and doesn't detract from my overall enjoyment of the episode (It is my favourite after all), but it always manages to take me out of the episode for a moment. Just a moment though.
Because the Jim/Pam/Roy triangle becomes such a huge part of the episode, it's easy to forget how funny Booze Cruise is. It starts with a classic Jim prank on Dwight where he puts all of his stuff in vending machines and doesn't let up from there. Jim and Pam feigning ignorance about the movie Titanic ("I think you're thinking of The Hunt For Red October" is one of my all-time favourite lines). One of Steve Carrell's best line deliveries as he responds to Daryl's suggestion that if the office was a ship the sales department would be the sails with an incredibly ignorant and condescending "Yes Daryl, The sales department makes sales". Captain Jack letting Dwight "steer" the ship and Dwight having no clue it's a fake wheel. Michael tearing up the dance floor. Even the bittersweetness of Pam and Roy setting a date gets a comic boost from Michael's power struggle with Captain Jack leading him to suggest that he give Pam away at her wedding. There is a lot of comic brilliance in this episode which helps keep it from getting bogged down in the melancholy, emotional moments while also making those moments more potent. The comedy does tone down once Jim and Pam have their moment and Pam reaffirms her engagement but it never goes away totally and it comes back in full force when Captain Jack sneaks off for a quickie with Meredith and Michael takes control.
The mundane setting of Dunder Mifflin means that big-scale comic set pieces were rare in The Office, particularly the early days (After Dwight's insane fire drill in season 5's Superbowl episode, they became more frequent). So when a frustrated and seasick Michael decides to finally kick off his presentation by announcing that the ship is sinking, the chaos of the moment was still a relative novelty. Even after seeing this episode dozens of times, the scene still never fails to be funny because of how well-constructed it is. We know what's going on and the annoyed employees of Dunder Mifflin know what's going on, but as Captain Jack reminded us at the beginning of the cruise, the Dunder Mifflin employees are not the only people on the boat, and once Michael tells people that "Captain Jack is gone", those poor confused souls stop listening and start panicking. It's a brilliant scene that builds and builds, getting more absurd until someone literally jumps overboard, paying off a joke quietly set up earlier when Captain Jack explained where the life preservers and emergency exits (anywhere over the side) were. Michael had good intentions with what he wanted to accomplish, but he let jealousy and poor judgement get the best of those intentions until they turned to cringe-worthy chaos the way they often do. So it's no surprise that Michael ultimately winds up in the brig, complaining that the boat wasn't as "corporate friendly as advertised" and unaware that he's done anything wrong.
If Booze Cruise were to end on a dark note with Michael's best intentions falling apart spectacularly and Jim miserable, it would still be one of the best episodes the show has ever done but it would probably not be my all-time favourite. It's a great, great episode but the thing that pushes it over the top is the ending. Trying to get away from the girl he loves and the girl he broke up with, Jim goes to the front of the ship where he finds Michael. They talk a bit about what a terrible night it's been and when Michael points out that at least Jim's friend got engaged (She was always engaged but Roy claimed the first one didn't count), Jim admits how he really feels to an extent. He says he used to have a big thing for Pam, much to the surprise of Michael who never would've put Jim and Pam together. This episode really is a tour de force for John Krasinski as he delivers yet another all-time great Jim performances just minutes after the last one. Before this episode Jim has never said a word about how he feels about Pam and now he's done it twice, and he's told Michael of all people, even if he tries to play it as in the past. We have never seen Jim so vulnerable before. This is big but it's nothing compared to what Michael says. "Well, if you like her so much, don't give up". It's a line Steve Carrell delivers with a shrug, said as casually as if they were discussing the weather and it throws Jim off. "She's engaged", he says but Michael shrugs that off too. "BFD. Engaged ain't married". Then the casualness is gone and suddenly Michael sounds like the inspirational speaker he's been trying to be all night. "Never, ever, ever give up" he says, and you can watch every one of those words slowly sink into Jim's face.
The thing about inspiration is that it's not something that can be planned or manufactured, it has to come from the heart. Michael wasn't trying to inspire Jim or prove what a great boss or friend he was. He simply reached out as a human being talking to another human being and tried to say something encouraging. He had given up on trying to inspire only to do it without even realizing what he had done and in that moment, we have our reason to believe in Jim and Pam back again because we have been given hope. With those words, the dark night suddenly turns into a hopeful one and a new friendship is forged between Jim and Michael that will persist until Michael finally left to get his own happy ending, his words paying off for him at last. As for Jim and Pam, Jim doesn't give up. He tries to distance himself from Pam but he still puts it all on the line on Casino Night. When he fails, he tries to. He moves away and he moves on but he doesn't really give up. Eventually he gets his chance. Eventually Jim and Pam date and marry and have children together like we all knew they would and it all comes back to that moment on the boat where he decided to not give up.
"Never, ever, ever give up". From the moment I saw Booze Cruise almost a decade ago that line hit hard and in the years since, it has stuck with me. The world can be a hard place and it's not easy to get the things you want most in life. It takes a lot of courage and a lot of effort and a lot of hope. The Office was not a hopeful show in the beginning. It was about compromise, wasting your potential away, giving up on your dreams, the drudgery of daily existence and the small things you did to try and make it better. It hid all this with a laugh and a smile and never explored it the way the British version did (And even the British version had a happy ending) but it was always under the surface. Even in the later seasons when the show became about finding happiness and family and beauty in the unlikeliest of places, that early darkness never truly went away. Booze Cruise is the most hopeful that The Office has been up to this point and it's remarkable because it suggests that even in your lowest moments, there's a light at the end of the tunnel if you're willing to find the strength to fight for it, to never, ever, ever give up. It's a powerful sentiment and one that we all need reminding of from time to time, especially in trying times like these where fear seems to have overrun everything. "Never, ever, ever give up". Things will get better, but they won't if you give up. You need to have hope. That's why Booze Cruise is my favourite episode of The Office and why it's the one I show to people trying to start watching the show. There's a lot to love about the episode, but in the end it all comes down to a pure and earnest hope that elevates everything else and makes it all better. The Office was great at being cringe-worthy and cynical, but when it looked through all that darkness and cringe to find a bit of honest hope, that's when it became special.
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