- Mike: My grandmother thought that a homosexual was a person who slept with one person their whole life. We were gonna let it slide but she kept telling the mailman she was a homosexual.
- Heidi Klum: We have a saying in Germany. It is better to have loved and lost than to engage in a land war with Russia in the winter.
- [the staff is concerned that the mayor may cheat on his wife]
- Mike: All right, everybody huddle up, close your eyes, I want to paint you a mental picture; the mayor is very vulnerable tonight, there are a lot of reporters here tonight, and also in attendance is a woman I will refer to simply as "The Shark", whereas the Mayor is like an older, slow-moving sea lion.
- Stuart: [French accent] I will stay aboard the Calypso, while my assistant, Mike, dive into the ocean to join in the life and death struggle between the shark and the noble sea lion.
- Mayor Winston: Mike, look out that window. We preside over the greatest city in the world.
- Mike: Sir, that's New Jersey.
- Nikki: [on the phone] No, mom, I'm not a lesbian. What? No, mom! I'm not a lesbian! I sleep with men. I sleep with lots of men. I'm a slut for God's sake!
- Mike: Look at Dick Clark. Not a grey hair on his head and he's as popular now as he was 100 years ago.
- Mike: Anybody read this? Bingo died.
- Karen: Ohh! Who's Bingo?
- Mike: Only the city's most decorated police dog.
- Nikki: Oh, yeah, right. He pulled that drowning kid out of the reservoir.
- James: And didn't he sniff out 10 kilos of cocaine at La Guardia?
- Mike: Yeah. Poor little guy didn't sleep for weeks after that.
- Deirdre: All right Blondie, listen up, here's the rules. You stay away from my man, or you and I are going to be co-starring in a play I like to call, "Deirdre the Prison Guard".
- Caitlin: No offense, but I'm not interested in your man, so why don't you just march those $12 pumps back to the trailer park and whip up some dinner for cousin dad?
- [Stuart is making fun of Carter's boyfriend, who is a boxer]
- Mike: That's right, Stuart. Taunt the professional ass kicker.
- [the Mayor is about to meet the President]
- Mayor Winston: What if I slap him?
- Caitlin: Why would you slap him?
- Mayor Winston: Well, you know, you tell yourself, "Don't slap the President, don't slap the President."
- [locked in Paul's trunk]
- Caitlin: I know you would enjoy this.
- Mike: What are you taking about? I am not enjoying this!
- Caitlin: Yes you are. I can feel "it."
- Mike: That's a tire iron.
- Caitlin: I don't care what sick name you call it! Get it off me!
- [Pulls out a tire iron]
- Mike: See.
- Caitlin: Ok. Then what is "that!
- Mike: Ok. I am a little excited.
- [Caitlin kissed Mike when there was turbulence]
- Mike: I get it. So whenever you're scared, you make out with guy nearest to you. Someday, you're going to make some mugger really happy.
- James: Stewart, I don't feel well. Knowing about Mike's mom and the Mayor is killing me.
- Stuart: James, secrets are power. You get something good like this, you sit on it. Right now, you leak it, it's just office gossip that makes everyone uncomfortable, BUT, in 20 years when Mike's running for President, this little gem gets me an ambassadorship to Sweden.
- James: What do I get?
- Stuart: Topless postcard from Sweden!
- Mayor Winston: I am not a child, and I *will not* be treated like one!
- Charlie: Sir, you forgot your shoes.
- Mayor Winston: I don't care.
- Roberta: Mr. Mayor, would you consider marching in the Gay Pride Parade this week?
- Mayor Winston: What, are you drunk?
- Carter: If the Deputy Mayor speaks in his office, and there are no cameras to hear, does he make a sound?
- Drew West: So, Randy... what's your favorite sexual position?
- Mayor Winston: Well, that's really not any of your business. However, I hear yours is "Man on top, woman in magazine."
- Mayor Winston: Are you sure this is the best title for my autobiography? "Winston On Winston"?
- Mike: Hey, as long there aren't two guys on the cover, I think we're okay.
- [Stuart visits Carter at his gym. Carter is wearing a headband]
- Stuart: Hey carter, is that headband to keep the bald out of your eyes?
- Paul: You know, I suck up to you until I'm out of suck and I'm out of up, and what do you do? You come in, you take my office! Why don't you say we switch roles for a minute, okay? How bout you kiss *my* ass for a while?