This kid is manipulating you. When you get mad, he cries. It’s been working for him for a while now, and at this point it’s like a dance. You both know all the steps, and when you say, “pick up your clothes”, the music starts and you both begin your dance.
You are the one who sees the problem, so it’s up to you to change it. You’re going to have turn into a broken record. Try having this conversation at breakfast: Tell him that if he wants to talk about “why” he has to do chores, it will only happen after the chores are done. Explain ahead of time what’s going to happen if he insists on arguing (that’s what he’s doing you know). Tell him that there are two options. He can sit in a corner or he can pick up his clothes (or whatever it is you’re asking him to do). When he’s done sitting, he must pick them up, and only then you’ll talk, or go for ice cream, or whatever treat you want to hold out to him as incentive.
He might cry at first, but YOU know you’re not mad at him (he knows it too in his heart), and it’s his own choices that makes him sit in his corner, or go without the ice cream, or cry for that matter. Keep it up until he gives in, not you. It may take a day or two, but if you are consistent, you’ll get the message across, and you will both be much happier. Above all, don’t get emotional yourself. Just be a broken record to him, and do not indulge in any other conversation with him other than “You must sit there for 8 minutes** and then you may pick up your clothes. If you don’t go into your room and pick up your clothes when the dinger goes off, you will go back to your corner and I’ll set the timer for 8 more minutes.”
**I chose 8 minutes because he’s 8 years old.