"How come he don't want me, man?"
- In "Papa's Got a Brand New Excuse," Will's deadbeat dad, Lou, comes back into Will's life after fourteen years, and Will tries his best to get to know him better. Even after Uncle Phil calls out Lou about not being there for him when he was a child, Will, for the first time in the show, outright defies Phil by telling him that he isn't his father. In the end, Lou's true colors show as he becomes more concerned over some new business and has to cancel a planned summer trip with Will. It's clear from their last talk together that Lou's not coming back—and Will doesn't want him to come back. Will tries to shake it off and launches into a monologue about all of the things he learned to do, and hopes to accomplish, without his father around to help him. He eventually breaks down as the weight of the situation fully hits him. Will finally just looks at Uncle Phil with the saddest look on his face and says one of the shortest, yet saddest lines ever uttered: "How come he don't want me, man?" Phil then gives him a Cooldown Hug. The camera then zooms in on the present that Will had bought for his father: an African-style wood carving of a father holding a young son.
Phil: I'm sorry, Will.
Will: You know what? Actually, this works out better for me. You know, the slimmies this summer come to class wearing next to nothing, you know what I'm saying?
Phil: Will, it's all right to be angry.
Will: Hey, why should I be mad?
I'm sayin' at least he said goodbye this time. I just wish I hadn't wasted my money buyin' this stupid
present! (takes the statue out of his bag)
Phil: I'm...I'm sorry. You know, if there was something that I could...
Will: [gradually getting angier] Hey, you know what? You ain't got to do nothing, Uncle Phil. You know, It ain't like I'm still five years old, you know? Ain't like I'm gonna be sittin' up every night askin' my mom "When's Daddy comin' home?," you know? Who needs him? Hey, he wasn't there to teach me how to shoot my first basket, but I learned, didn't I? And I got pretty damn good at it, too, didn't I, Uncle Phil?
Phil: Yeah, you did.
Got through my first date without him, right? I learned how to drive, I learned how to shave, I learned how to fight without him, I had 14
great birthdays without him! He never even sent me a damn card! TO HELL WITH HIM!!!
[Phil breathes like he's about to cry]
Will: I didn't need him then, and I don't need him now.
Phil: Will? Will?
Will: No, you know what, Uncle Phil? I'm-a get through college without him, I'm-a get a great job without him, I'm-a marry me a beautiful honey and I'm havin' me a whole bunch of kids. I'm-a be a better father than he ever was! And I sure as hell don't need him for that, 'CAUSE AIN'T A DAMN THING HE COULD EVER TEACH ME ABOUT HOW TO LOVE MY KIDS!! (long pause; Will tears up) How come he don't want me, man? (he and Phil embrace)
- In "Bullets Over Bel Air," Will takes a bullet for Carlton when the two are mugged while withdrawing money from an ATM. After seeing Will hurt so badly, Carlton's feelings of helplessness push him over the edge, and he buys a gun and even brings it with him to the hospital. Will ends up begging Carlton to get rid of it so that he doesn't intentionally or accidentally hurt someone in the same way that Will was. After convincing Carlton to give up the gun, Will breaks down in tears. Link
- And then there was the way in which Carlton finally relented in giving the gun. Will tried joking about his situation, he tried to calm Carlton down, and he tried to reason with him. None of that worked. Will had to use a desperate last-resort You Owe Me. You can hear his voice break as he was essentially begging for the gun.
- And when Will checks if the gun was indeed loaded, he finds that, yes, Carlton actually bought a gun and loaded it with ammo with the intent to shoot someone out of self-defense, or to defend a loved one, if the need came for it. This is Carlton we're talking about.
- This commentary makes the moment even sadder.
You gotta think, the whole concept of this show was Will growing up in a bad neighborhood where shit like this happened all the time, and Carlton grew up in a life of privilege and sheltered from this kind of life, and I think Will was crying because he came so close to seeing Carlton go down the wrong path and end up like some of his friends back in Philly.
- After Jazz inadvertently jeopardizes Phil's chances at being a judge, Will blows up at him and tells him to leave.
Will: So, as of now, this friendship is over. You're not welcome here, so I'd like it if you just got the hell outta my crib!
Will: You're not even worth it, man.
- Most of the Series Finale, for long-time viewers of the show. Even Carlton's So Bad, It's Good dancing to Tom Jones, because it was the last time we'd ever see it...and even more so when it was Will's idea and he actually joined in! In this case, though, you'll most likely be laughing your head off and tearing up at the same time.
- "Home is Where the Heart Attack Is"
- Will tearfully admitting that he "caused" Phil's heart attack by giving him a cheeseburger he bribed him to buy.
- Carlton being afraid to see his father in such a vulnerable position, saying that he's like Superman to him. This one is softened by Mood Whiplash, though it still works pretty well in the context (one can see it as Phil not wanting to see his son so sad about his state):
Phil: And cheesecake is my Kryptonite, huh?
- This is also the first time Will ever talked about his own worthless father and uses that to push Carlton into seeing Phil.
Carlton: Look, I don't wanna see my father with tubes up his nose, okay?
Will: There's gonna come a time when all he has is tubes up his nose.
Carlton: (voice breaking) NOT MY FATHER!!!
- And the whole thing becomes even harder to watch after James Avery's death during heart surgery.
- "Mistaken Identity" has Carlton having his first encounter with racial discrimination when he's pulled over by a cop for driving a Mercedes in a white neighborhood. Carlton tries to deny the racism involved and justify the cop's intentions as Will tries to tell him that the justice system has flaws and that he will experience racism his whole life.
Carlton: Dad, if you were a policeman and you saw a car driving two miles an hour, wouldn't you stop it?
Carlton: (to himself) ...I would stop it.
- When Hilary finally comes to terms with Trevor's death and laments that she didn't get to say goodbye to him before the bungee accident. Will comes down and tells her that it's never too late to say goodbye and that Trevor is still there in her heart. After Will leaves, Hilary stops for a moment to say to the stars "Goodbye, Trevor."
- ...she then walks into a door, for some final comedy and serious Mood Whiplash.
- The ending of the episode "Just Say Yo": . Will confesses to Uncle Phil that the amphetamines Carlton took were his. Uncle Phil assumes Will was getting into drugs and forces Will to confess the truth to everyone in the house. What follows is Will tearfully confessing of his struggles for the week (several tests, basketball practice, and his girlfriend) and a classmate gave him the drugs (which he never took to begin with).
Will: All I know, is that someone I care about, that I love a whole lot, could be dead right now. And it'd be all my fault....
- Will's crying is just painful to hear, especially when Uncle Phil, who ended up assuming Will was getting into drugs, slowly embraces him.
- Not helping is the fact that just before this confession, Phil intended to give Will season tickets to a game that he'd been saving for him for a long while. It's Will's guilt at being rewarded for saving his cousin who he accidentally allowed to overdose in the first place that prompts him to come clean to Uncle Phil.
- In the 1st season, Trey, one of Will's buddies from Philly, comes for a visit. He's a nice guy and Hilary is smitten with him, but Vivian dislikes him due to the fact that he has no real goals in life. Later on, Will calls her out for her attitude towards him and explains that Trey didn't have the chance that Will did, that he looked out for Will and made sure he studied and did well in school at the cost of his own school life, and that if it wasn't for him, Will may have fallen in with a wrong crowd, causing Vivian to realize she was wrong to judge him like that.
- "Asses to Ashes", in which Will told off Judge Robertson, causing him to have a fatal heart attack, was mostly Black Comedy, but Will's remorse over the man's death is quite saddening.
- "Hex and the Single Guy" saw Will pissing off Scorpius, a flamboyant psychic who conducts a seance to contact Hilary's late boyfriend Trevor, who ends up hexing the whole family as a result. When Will returns the next day to have him remove the hex, the inside of Scorpius' house is completely redone, and Scorpius himself, now an unassuming man named Ralph Scorpius, claims to have no memory of Will from the night before and assumes he's robbing him. Will becomes convinced he's going insane and ends up having a Heroic BSoD, tearfully begging Scorpius to remove the hex, and while the scenario is Played for Laughs it doesn't make Will's breakdown any less heartwrenching to see.
- The episode "It's a Wonderful Lie" in Season 5 has a lot of conflict in it, with the focus characters of the episode struggling with trust. Ashley in particular lies to her parents, is discovered at a party full of college boys and runs away from home for a short time. When she faces up to her parents about it at the end of the episode, Phil gets too angry to lecture her properly and leaves Vivian to talk to Ashley about it. It's one of the few times that Daphne Maxwell Reid gets an intense scene as Vivian, and she nails it. Ashley clearly realises during the discussion how much she betrayed and hurt them, but Vivian remains cold and distant while gently and logically reprimanding her about how fragile trust can be. You can see and hear how much Vivian doesn't like speaking to her daughter like this and it's very clear that Ashley regrets what she did, so right before Ashley leaves as she's sent to her room, Vivian calls to her with a shaking voice. She walks over to Ashley and the two of them embrace as Ashley breaks down crying and apologises.
- In "The Alma Matters" Will and Carlton are both interviewed by a Princeton official scouting for interested applicants, and so naturally Carlton has prepared for his make-or-break case for acceptance. Will's record does little to impress the man until he starts playing it cool with his usual antics, which greatly amuses the representative and earns Will a conditional acceptance, much to Carlton's shock. Not believing it, he springs the same act upon the man, who is convinced that Carlton is crazy and turns him down flat. Carlton panics and tries to convince him otherwise, and when this fails, he actually threatens the man on an impulse and catches his mistake too late. Getting himself suspended, Carlton tries to pretend nothing is wrong and lies to everybody that he's been accepted with a full scholarship, much to the joy of everybody, especially Uncle Phil. And then they receive a call from school:
Uncle Phil: Hey, I just heard the good news! What? Well, how can he be suspended? He just got a full scholarship! (...) I'll, uh....I'll call you back.
Uncle Phil: Carlton.....Tell me you didn't threaten to kill the man from Princeton.
Vivian: Oh, my God!
- Carlton eventually makes peace with his father over the incident, but the pain and disappointment in Carlton's face as he sees how badly he hurt his family as well as himself is very raw, knowing he just blew his lifelong goal of attending Princeton as his father did. And at the time, it certainly looked like he would never be granted a second chance...
- The rest of the episode before they make up focuses on Carlton moping over his screwup and wishing he wasn't born. It takes a visit from his guardian angel Tom Jones to make his realize his worth as a person and to his whole family.
- Really, this episode is the culmination of a theme that had been part of the show since the start, the way Will seems to effortlessly charm his way through everything in a way Carlton can't even hope to match, but this is the first time Carlton openly expresses how much it frustrates him. Sure, Carlton is disciplined and a hard worker, and there's always value in that, but Will has natural people skills, and you can't teach those, you either have them or you don't. And Carlton doesn't. And this time it looks to him like Will got his dream school without even wanting it.
- Calton losing his virginity in "It's Better to Have Loved and Lost It..." — First, he's made fun of Will and their friends for being the only one among them to not have had sex, and is further ridiculed when he explains he's waiting for the right person. And he seemingly does in Jo Ann. They have sex after a date and Carlton is thrilled not only because of the sex but because he believes he's finally met the woman of his dreams...only to later find out she's married and was using him to get over her issues with her husband before coldly telling that the sex was a one time thing. Carlton is crushed to say the least.