
I love the opening hook in Outlaws, a chilling scene where a toddler version of Sawyer witnesses his parents' gruesome death.
On the island, Sawyer's pursuit of the boar would've been effective merely as comic relief but Drew Goddard took it a step further. Sawyer would occasionally regress in future seasons, but Outlaws was the episode that smoothed out some of his roughest edges.
Three scenes make Outlaws a classic:
1. The "I Never" campfire scene with Sawyer and Kate. It seems fitting that these two would need a juvenile college game as a pretext for confessions. Goddard does a phenomenal job of making the game smoothly progress from trivial matters to bombshells.
2. Locke's anecdote about his foster mother and the stray dog. Given Sawyer was convinced that a boar had an axe to grind, the story obviously resonated with him. Locke's grin says it all.
3. Sawyer and Christian at the bar. At this point the audience is noticing different Lostie connections, and this conversation takes it to the next level.
Considering most of the episode was dedicated to humanizing Sawyer, it's mildly surprising to see him shoot a man in cold blood near the end. It was interesting, perhaps even a bit rewarding, to see Sawyer finally get conned though. It does indeed come back around.

On one hand it's true that Josh Holloway didn't display much of a range with his perpetual scowl and cold stare. But one scene redeemed him to an extent: "I Never" with Kate. His delivery of certain lines, especially "do I gotta drink for each [one night stand]?", had me grinning from ear to ear.
Despite his narrow character definition in Season 1, Holloway still nailed his one-liners regardless of the circumstances. Even at the peak of his frustation in Outlaws, lamenting that the boar was "harrassing" him had me in stitches.
Evangeline Lilly and Terry O'Quinn were the ideal choices to accompany Sawyer on his hunt. Lilly and Holloway are clearly capable of selling sexual tension, while anecdotes just aren't the same coming from anybody but Terry O'Quinn.
Robert Patrick was solid as expected, even if I personally can't seem to separate him from the role of John Doggett and/or T-1000.

No surprises here, Bender does a great job in sensing when a scene can/should run long, when to close in on a character and when to back away. Scenes like "I Never" and the Sawyer/Christian conversation are rare in the LOST world, both in terms of overall length and the sheer amount of dialogue.
The opening scene is brilliant, allowing us to witness the horror of a murder-suicide from the perspective of young Sawyer under the bed. No guts and no gore but plenty of horror.
Bonus points for the slow-mo of Sawyer walking away from Sayid after discussing the whispers. I love slow-mos as a transition to flashbacks, and I'm not sure I can even articulate the reasons. It just feels right.

Even if one doesn't appreciate the magnitude of the "I Never" scene, it's undeniable that Sawyer's conversation with Christian is a significant moment in the series and thus lends itself to repeated viewings.
The flashback storyline obviously has a significant drop-off in shock value after first watch, but it's nowhere near boring and it maintains a relatively brisk pace all the way through.
In terms of the episode's importance in the overall series: that's where it gets a bit difficult. For starters, given Sawyer's arc across the entire series it's difficult to say whether any of his flashbacks amounted to anything. One could argue he was just as guilty of cowardice and selfishness in late Season 6 as he was any time before that, so one questions whether episodes designed to humanize him are an exercise in futility.
More importantly, Outlaws introduces a recurring theme of animals appearing on the island and haunting certain Losties with a guilty conscience. There are plenty of theories about who/what the animals were: Man in Black, Jacob, manifestations of the victims, or just... animals. All of those theories can be convincing with the proper supporting evidence, but I wish the writers themselves had provided a slightly more solid narrative on this point. It's a little frustrating seeing the Sawyer/boar confrontation while knowing I'll never have a definitive answer on where the writers were originally going with it.

You'll find that I'm not the biggest Sawyer or Kate fan, yet this episode was so well-written and directed that I couldn't help but get absorbed. On paper this episode looks to be way too heavy on dialogue, but as many times as I've seen it I've never felt the scenes collapses under their own weight.
It's also worth noting that while Michael Giacchino is a musical genius, Outlaws is proof that sometimes less is more. The "I Never" and Sawyer/Christian scenes are very long by LOST standards, yet no music is needed to sell the weight of the moment. The dialogue stands on its own merits and the scenes are memorable as a result.
I can't say I was emotionally charged by portion of the episode except the opening scene, but I could definitely appreciate the intent of humanizing Sawyer and I was willing to go along for the ride.