For one thing, I can see what Roddenberry was up to in creating him. He serves two functions. Firstly, he is the "Mary Sue" character that allows young people to imagine themselves on the ship with all the super-heroic Starfleet officers. Second, he is the wunderkind that allows young nerds to imagine that "it gets better." Now, it could be that for some, these two ideas work at cross purposes - one of the most commonly leveled accusations against the character is that he "saves the day" too much or is annoyingly smart. How can we identify with a character who is so exceptional? And to some degree this is fair. But then, some of us were exceptional children, nerds, geeks, spelling bee champs, and so on. So it is at least possible that we might still find Wesley comforting and charming to watch.
OK, all that said, Let's kick things off with Honorable Mentions.
Do I... have to take off my sweater to play this... game?
I have to start with Justice. It's kind of a terrible episode, but in that "so bad it's good" way. Why does it rate an honorable mention? Because of how Wil Wheaton described trying to conceal his boner throughout the shoot. Just imagining a teen-aged boy surrounded by all these tanned, oily, half-naked actresses who talk about sex really boosts one's appreciation for the art of acting.
Even if everyone else hates you, Wesley, I still love you.
Seeing Wesley watch his father's holo-message to him was quite moving. Not a Wesley episode per se, but still a great one.
It was obviously the pantsuit that piqued young Wesley's interest.
If nothing else, this episode showed that dorks can be sweet and charming, and that being the only person of analogous age around is a real aphrodisiac. He shows a shocking lack of foresight when he gets weirded out by her shape-shifting abilities, however. She's a shape-shifter who can look like any girl you want, Wes! COME ON!
Coming of Age
I am so glad I wore my rainbow ensemble for the big test today!
Wesley faces his fear of making a fatal command decision, in the unduly elaborate and detailed "psych test" that the Academy apparently foists upon all its candidates. He also acts like a racist who thinks all Benzites look alike. But who's counting?
OK, now the list proper:
5. The Game
I don't want to say this comes down simply to "Wes gets to bang Ashley Judd," but... come on. Wes gets to bang Ashley Judd! This has to rate as a high water mark for any character, given her very high showing on our list of Trek's hottest women.. There is also a lot of fun stuff in this show, with Wesley walking in on his mom's masturbatory game session, lots of sciencey stuff, being chased around the ship and evading capture, and having his eyelids held open by Commander Riker.
4. Where No One Has Gone Before
This video makes me feel strange... but also good!
So... Wesley is Mozart. All right. Maybe some people find this to be the show that went too far, that broke the camel's back, and so on. But one thing we've always said here on Treknobabble is you can't and shouldn't punish an episode for the sins of those that follow it. On its own terms, this episode is really good, and it's a good showcase for Wesley's special nature. He builds a nice rapport with the Traveler, immediately susses out that Kozinski is a twit while the adults don't, and plumbs the depths of time and space. Cool!
3. Final Mission
Oh, who am I kidding. The boat house was the time!
Although Wesley kind of acts like a tool in the way he treats Captain Dergo, it is coming from a place of love - his love for Captain Picard. This is a really sweet show in which Wesley wants not only to save his father-figure, but also to make him proud. His eventual farewell is very moving, both with his mother and the Captain.
2. The First Duty
His bouffant is even taller than mine!
Some times the best moments for a character are when they are at their lowest. And I think this episode represent's Wesley's low point. All of those expectations and pressures seem to have caught up with him. He is in the Academy, but is pushed to excel by a charismatic fellow student. In the process, one of his friends dies, and for the bulk of this show, Wes is (at least outwardly) convinced that lying about it is his best course of action. Thankfully, Picard lays the verbal smack down on him, resetting his moral compass. But the damage to his reputation and career are done. I like this quite a bit more than the follow-up, "Journey's End," mainly because he seemed like such a bitter douche in that show. Here, he is relatable and sympathetic, and I think any viewer will find his or herself pulling for him to somehow succeed.
So what's it like having such a MILF for a mom, Wes?
This is not a great Wesley episode simply because of the return of his mother. But her return does precipitate a very nice look at his character. Wesley is beset by the high expectations of every adult around him, and often tries very hard to exceed them, at the expense of his own feelings. When he meets a man, Dr. Stubbs, who seems to have followed this path to a bitter, unpleasant adult life, Wesley is given occasion to re-evaluate. But he also has to fix his own nanite screw-up along the way. This episode goes a long way towards humanizing Wesley's character, and is a lot of fun overall.