(As usual, many spoilers here.)
5. "You guys got any milk?"
If Lost were somehow transformed into a rap battle (I'm thinking something along the lines of Wild 'n Out, or whatever that show really was), this scene would send all the Henry Gale (later known as Ben Linus, because, well, that was his name) supporters into a crazed frenzy. Unfortunately for Ben, I'm not sure he had any at this point in the show. Retrospectively, this was a total badass move by letting Jack and Locke in on his possible secret of luring some Losties into the forest to kidnap them. One of my favorite dynamics of the show was between Ben/Henry and Locke, and there was no better scene to say "hey, this guy means business" than this one.
4. "Red Sox fans have longed to hear it..."
Okay, so maybe this wasn't badass, but it was still one of the most memorable moments in the show. Absolute power move by the writers to find a way to get this in the show. Out of all the jokes they could make with literally anything, they went with the damned Red Sox never winning the World Series, and then they won it. And then Ben tormented Jack with a video of the last out. Power moves all around, except for Jack, who just received a huge "screw you" from the person whom he had hostage not long before.
3. "I was wrong."
It's not a coincidence that four of these five scenes will have been from Seasons Two and Three, because that's when the show was really diving into these characters. (It was also the only time the show was actually good.) The general trajectory of meaning in this show went from "let's decide to push or not push a button for reasons unbeknownst to us" to "this is secretly about good and evil and has been the entire time." The former was still a great conversation to be had, and there are a handful of amazing scenes that I could have pulled out for this one. But it all came together here, during arguably the best season finale (Season Two).
2. The blast door map
I really wanted to give this the top spot in my top five moments, but it can't beat out the greatest conversation in the entire series. What honor this scene does have lies in the fact that every single person went to bed that night with this blast door map in their dreams. This would have put me in 8th grade back in the day, back when evil doors and blacklight paint were totally viable reasons to not be able to sleep. This was done tremendously by the writers as well, because we were experiencing this at the same time that Locke was, an awesome technique that Lost seemed to rely on. We often knew just as much as the characters did (which was usually nothing), and because of that, their emotional experiences during events were only fueling our own as viewers. No better scene to capture that than this one.
1. "Always nice talking to you, Jacob."
If there was anything about Season Five that was good, it was this scene in the season finale. Watching this scene before and after the show was over were completely different experiences. After you've seen Season Six, you know that this is about good and evil, and Jacob and the Man in Black are the two representatives, respectively, and after we've spent the entire sixth season watching a war waged between these two, we return to this scene and realize that they're both probably right. Watching this for the first time though, you're experiencing it something along the lines of "OH MY GOD THAT'S JACOB FINALLY HE EXISTS WHO'S THAT OTHER GUY WHY DOES HE WANT TO KILL HIM WHY IS THE FOUR-TOED STATUE THERE WHAT SHIP IS THAT OH MY GOD" and then nothing else really matters at that point in your life. (Unless that was just me.) In classic Lost fashion, a question (is Jacob even real?) is answered (yes) with several other questions (why is everything we thought we knew now destroyed?). Huge props to Michael Giacchino and the music in this scene. Absolutely adds to the dramatic effect and how badass this scene is, and more relevantly, how important this scene was to the show. If you look up any decently-written list of Lost moments, you'll find this scene on there in some capacity.
what about "not penny's boat"? that is my most memorable Lost moment.... mom.
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