Jack: Never go with a hippie to a second location.

Jack: New York gives us a tax break for employing sex offenders. It's a terrible program.
[when Jack arrives at Kaylee's school to confront her]

Jack: Now let me hear you say the seven most important words in the American judicial system.
Frank: My client has no memory of that.
Jack: I also would have accepted "You can't prove that's the governor's semen."

Jack: Oh, Diana, you're here, I thought you'd be at the house.
Diana: Oh yes, I dropped my bags off and shook hands with the baby but I wanted to come talk to you about Avery's situation.

Jack: Ongoing train wreck aside, I love this idea; it's great synergy. By putting a TV actress into the movie world we can promote both. It's like how we're including a Heroes DVD with every missile system we sell.

Jack: Pete and I are having a little college night.
Liz: Oh yeah you want to see me shotgun this?
[Liz begins shoving an entire pizza into her mouth]
Jack: Oh God! She means the pizza!
Pete: She's unhinging her jaw!

Jack: She's courting the youth vote. That means she's desperate.
Jonathan: My generation never votes. It interferes with talking about ourselves all the time.

Jack: So what are you gonna do with your money? Put it into a 401(k)?
Liz: Yeah, I gotta get one of those.
Jack: What?! Where do you invest your money, Lemon?
Liz: I've got like twelve grand in checking.
Jack: Are you an immigrant?

Jack: That's what I'm talking about, empathy. It's about as useless as the Winter Olympics... this February on NBC.

Jack: That's where Donaghy Estates comes in. Now as you may have read in Robert Parker's Wine Newsletter, "Donaghy Estates tastes like the urine of Satan after a hefty portion of asparagus."

Jack: The bubble isn't always a bad thing. Look at me. I turned out okay.
Liz: Jack, I want you to pay close attention to the following over-the-top eye roll. [rolls eyes] Oh, brother.
Jack: Lemon, I don't share this often, but this is a photo of me when I was 25 years old.
Liz: What the what?! You have a Superman chest!
Jack: I know.
Liz: Oh my God, the lady will have two tickets to the gun show! Your eyes are so much bluer... what happened to your eyes?
Jack: My point is, Lemon, the bubble doesn't last forever, so get in there with Drew and enjoy those perks while you can.
Liz: Can I keep that?
Jack: No. It's my only copy.

Jack: The stutter got so bad I was taken out of my grade and put in the special class, held in the boiler room. My only other classmate was named Gilly. He'd fallen though the ice as a child and was technically dead for 57 minutes. They taught us to sweep sawdust so we could find work at a mill. Of course I overcame the stutter in three languages. On to Princeton, Harvard, the top of the business world. I thought I blocked this out, but a thing like this brings back emotions.
Liz: I'm so sorry.
Jack: I feel like I'm back in that boiler room, making little piles of sawdust while Gilly plays with himself in the corner...

Jack: The television audience doesn't want your elitist, east coast, alternative, intellectual, left wing...
Liz: Just say Jewish Jack, this is taking forever.

Jack: The UN is useless, the State Department is full of Democrats, and as it turns out Amnesty International is nothing but a company that makes and sells candles...
Liz: That explains all the vigils!

Jack: The world is made by those who control their own destiny. It isn't made by those who don't do, it's made by those who do do. Which is what made me the man I am, I do do.
Liz: Yeah, you do.
Jack: Grow up, Lemon.