“You’re kidding [that you were faithful to your wife]? Really? What’s that all about?… I was actually faithful to my wife for many years, until I realized the marriage wasn’t gonna work…

“[Ivana‘s accent] was like the Chinese torture. You know, the water drops on your head.”
- 1993

“I didn’t say [‘you have to treat women like shit’]. The woman’s a liar, extremely unattractive, lots of problems because of her looks…

“People say, ‘How can you say such a thing?’ but there’s a truth in it, in a modified form. Psychologists will tell you that some women want to be treated with respect, others differently. I tell friends who treat their wives magnificently, get treated like crap in return, ‘Be rougher and you’ll see a different relationship.’…

“Putting your wife to work is a very dangerous thing — the single biggest reason my marriage stopped being good… I don’t want to sound like a chauvinist, but when I come home at night and dinner’s not ready I go through the roof. But I got handed casino numbers. After 12 hours dealing with my companies, I didn’t want to talk business. I can instantaneously shut it off, my survival mechanism. But she’d be yelling into the phone with the casino; I didn’t want my wife shouting like that. Ivana had a great softness that disappeared. She became an executive, not a wife…

“I’m a great starmaker, which I’ve done with Ivana and Marla. I liked that. But once they are a star, the fun is over for me. It’s the creation process, like creating a building. It’s sad…

“Marla doesn’t want to sign [a prenuptial agreement] but she has to from my standpoint… I look at everything like a deal… If our marriage doesn’t work out, I don’t want to go through five years of lawyers, legal fees. If I give more [than the $1M I negotiated her down to], I want to make the decision, not some court saying, ‘You agreed to pay X — and will.’ Ivana challenged our pre-nup for three years, ending up with the original settlement.”
- 1994

“[Miss Universe Alicia Machado is] an eating machine… She weighed 118 pounds or 117 pounds and she went to 160 or 170. So this is somebody that likes to eat.”

“Miss Piggy”
- 1996

“The [1997 Miss Universe] pageant in Miami Beach, my first as owner, was a huge success. We’d sold out the house; it was a mob scene. From my position offstage, I was able to glance up to the greenroom occasionally. I could just see Alicia Machado, the current Miss Universe, sitting there plumply. God, what problems I had with this woman. First, she wins. Second, she gains fifty pounds. Third, I urge the committee not to fire her. Fourth, I go to the gym with her, in a show of support. Final act: She trashes me in The Washington Post — after I stood by her the entire time. What’s wrong with this picture? Anyway, the best part about the evening was the knowledge that next year, she would no longer be Miss Universe…

“Women are far stronger than men. Their sex drive makes us look like babies. Some women try to portray themselves as being of the weaker sex, but don’t believe it for a minute…

“Women have one of the great acts of all time. The smart ones act very feminine and needy, but inside they are real killers. The person who came up with the expression ‘the weaker sex’ was either very naive or had to be kidding. I have seen women manipulate men with just a twitch of their eye — or perhaps another body part…

“They are far worse than men, far more aggressive, and boy, can they be smart. Let’s give credit where credit is due, and let’s salute women for their tremendous power, which most men are afraid to admit they have…

“My big mistake with Ivana was taking her out of the role of wife and allowing her to run one of my casinos in Atlantic City, then the Plaza Hotel. The problem was, work was all she wanted to talk about. When I got home at night, rather than talking about the softer subjects of life, she wanted to tell me how well the Plaza was doing, or what a great day the casino had. I really appreciated all her efforts, but it was just too much… I will never again give a wife responsibility within my business. Ivana worked very hard, and I appreciated the effort, but I soon began to realize that I was married to a businessperson rather than a wife…

“Marla was always wanting me to spend more time with her. ‘Why can’t you be home at five o’clock like other husbands?’ she would ask. Sometimes, when I was in the wrong mood, I would give a very materialistic answer. ‘Look, I like working. You don’t mind traveling around in beautiful helicopters and airplanes, and you don’t mind living at the top of Trump Tower, or at Mar-a-Lago, or traveling to the best hotels, or shopping in the best stores and never having to worry about money, do you? … I always viewed her whys as being very selfish…

“The prenuptial agreement… There are basically three types of women and reactions. One is the good woman who very much loves her future husband, solely for himself, but refuses to sign the agreement on principle. I fully understand this, but the man should take a pass anyway and find someone else. The other is the calculating woman who refuses to sign the prenuptial agreement because she is expecting to take advantage of the poor, unsuspecting sucker she’s got in her grasp. There is also the woman who will openly and quickly sign a prenuptial agreement in order to make a quick hit and take the money given to her.”
- 1997

“Often, I will tell friends whose wives are constantly nagging them about this or that that they’re better off leaving and cutting their losses. I’m not a great believer in always trying to work things out, because it just doesn’t happen that way. For a man to be successful he needs support at home, just like my father had from my mother, not someone who is always griping and bitching. When a man has to endure a woman who is not supportive and complains constantly about his not being home enough or not being attentive enough, he will not be very successful unless he is able to cut the cord…

“[I told a friend whose wife said he was] working too hard and too long and wasn’t devoting enough time or energy to her [to divorce her]. If he doesn’t lose the ballbreaker, his career will go nowhere.”
- 1997

“I look at this picture that they have in the magazine [of Cameron Diaz]. And she looks magnificent… She is much different looking in person…

“A number of years ago [Michelle Pfeiffer] was one of the — she was really beautiful… I don’t find her that sexy right now…

“Lady Di was truly a woman with great beauty. I’ve seen her a couple of times. [I ‘would have slept with her’] without even hesitation… She was supermodel beautiful. She had the height, she had the beauty, she had the skin – the whole thing. She was crazy, but these are minor details.
- May 18, 2000

“Your intern is incredible, Julie. It’s her first day… Get her out here. Get her out here. She’s amazing. Get her out, Howard [Stern]. This could be a real — this could be a star. Come here, Julie… Yes [she’s a ‘hot chick’], look at the face… She could be The Apprentice… She could like me a lot…

“Woman, I can tell [what they weigh] within half a pound…

“I really like J. Lo, but that ass is…

“The three hottest [women today aside from Melania]…Keira Knightley she’s just a kid [19]… But she’s absolutely beautiful…

“Now somebody who a lot of people don’t give credit to. But in actuality is a really beautiful, really beautiful. Paris Hilton. I’ve known Paris Hilton from the time she’s 12, her parents are friends of mine, and the first time I saw her she walked into the room and I said, ‘Who the hell is that?’. I’ve never been into that. That’s sort of always stuck around that 25 category… At 12 she was beautiful. But honestly you know, Paris gets knocked in this and that but she’s very beautiful. She’s gone flawless…

“I have seen [the Paris Hilton sex video]. I thought it was just yeah…

“You know who’s one of the great beauties of the world — according to everybody — and I helped create her? Ivanka. My daughter, Ivanka. She’s 6 feet tall, she’s got the best body. She made a lot of money as a model—a tremendous amount… She’s considered one of the most beautiful women. And she really is, she’s a great beauty.”
- Jan 7, 2004

“All of the women on The Apprentice flirted with me — consciously or unconsciously. That’s to be expected…

“It’s certainly not groundbreaking news that the early victories by the women on ‘The Apprentice’ were, to a very large extent, dependent on their sex appeal. I believe we’re all equal except women still have to try harder and they know it. They will do what they have to do to get the job done and will not necessarily be demure about it.”
- 2004

“Ivanka‘s beautiful… Yeah [you can say she’s a ‘piece of ass’].”
- Sept 23, 2004

“There’s something there [with Lindsay Lohan, then 18], right? But you have to like freckles. I’ve seen a — you know a close-up of her chest. And a lot of freckles…

“She’s probably deeply troubled and therefore great in bed. How come the deeply troubled women, you know, deeply, deeply troubled, they’re always the best in bed…

“Now the good news I own the Miss Universe pageant, so I get used to a good looking women. But the most beautiful women — I go out to do Jay Leno Show. And women come up to me, gorgeous actresses well-known actresses, and they look at me and they say, ‘I had no idea how handsome you were.’ And then you know they’re full of crap when they say and your hair is absolutely beautiful. Okay. See, when they start to-… So what happens is I go — I go through this, and I have hundreds and hundreds of people coming up to me, and I’ve really been a good boy.”
- Dec 15, 2004

“Miss America is dead because they don’t know what they are doing… Number one, they have a talent contest. Nobody cares about the talent. There’s only one talent you care about, and that’s the look talent. You don’t give a shit if a girl can play a violin like the greatest violinist in the world. You want to know what does she look like…

“It’s all in the hunt and once you get it, it loses some of its energy. I think competitive, successful men feel that way about women. Don’t you agree? Really, don’t you agree?…

“My favorite part [of Pulp Fiction] is when Sam has his gun out in the diner and he tells the guy to tell his girlfriend to shut up. Tell that bitch to be cool. Say: Bitch be cool. I love those lines.”
- 2005

“[If Melania had become horribly disfigured in a car accident] how did the breasts look?… That’s important… If something negative happened to Melania, I would be there for her 100%… She will always remain beautiful. Of course, car accidents do, do wonders…

“I like kids. I mean, I won’t do anything to take care of them. She’ll think I’ll supply the funds and she will take care of the kids, right?…

“It’s not like I’m going to be walking the kids down Central Park… She would take care — great care of the child without my having to do very much… [School events are] not really my scene. I have to tell you it’s not my thing. But, she’ll be — she’ll be very good about it. I think I’ll have to go to a minimum of school plays…

“Actually I’ve always been a very good father. If you ask my children who’s been the best, I think a lot of them would choose me. But I’ve always been a really good father and I’ve liked being a father but I don’t do too much work…

“I never comment on [whether I’ve had sex with pageant contestants]… I’ve owned the pageant for a long time. You know the Miss Universe pageant is amazing because you have ninety seven countries and every… I mean no matter what you looking for, you have them in… [Having sex with pageant contestants] could be a conflict of interest. But you know it’s the kind of thing you worry about later… You could also say, ‘It’s the owner of the pageant it’s your obligation to [have sex with him]’…

“The funniest is that I’ll go backstage before a show. And everyone is getting dressed and ready, and everything else and then there are no men anywhere, and I’m allowed to go in because I’m the owner of the pageant and therefore I’m inspecting it. You know I’m inspecting it, I wanna make sure that everything is good. You know, the dresses. ‘Is everyone okay?’ You know, they’re standing there with no clothes. ‘Is everybody okay?’ And you see these incredible looking women, and so, I sort of get away with things like that.…

“You know, when I bought Miss USA, Miss Universe it was a sick puppy… And then I made sure that the women were really beautiful because they were getting a little bit not as beautiful and it’s a sad thing to say…

“I actually went on ‘The Today Show’ with Katie Couric a while ago six years ago and we had a woman running the pageant who was really into the whole thing of education and everything, and I said, ‘Look, if you’re looking for a rocket scientist, don’t turn in tonight. But, if you’re looking for a really beautiful woman, you should watch.’ The head of the Miss Universe contest blew up, she went crazy ‘How dare you say that? That was a terrible thing to say.’ You know in other words, Howie, the women are really, really beautiful…

“I’ve made it hot. I’m very proud of that. And people said, ‘How did you do that?’ And I jokingly said the heels got higher and the bathing suits got smaller. And then they said I was joking, And then I realized, ‘Why am I defending myself because that happened?’ [The bikinis] are almost thong-like. You know NBC, if it were up to me they’d get smaller. But NBC has certain standards so they’re sort of thong-like… All they do is walk back and forth. We put lots of bathing suits on… [The ‘girls’ are] anywhere from 18 to 23, 24…

“I’ll have a monopoly on beauty pageants. It doesn’t do me any good though because I’m married. Happily married.”
- April 11, 2005

“I did try and fuck her. She was married… I moved on her like a bitch. But I couldn’t get there. And she was married. Then all of a sudden I see her, she’s now got the big phony tits and everything. She’s totally changed her look…

“Yeah, that’s her. With the gold. I better use some Tic Tacs just in case I start kissing her. You know, I’m automatically attracted to beautiful — I just start kissing them. It’s like a magnet. Just kiss. I don’t even wait. And when you’re a star, they let you do it. You can do anything… Grab ’em by the pussy. You can do anything.”
- Sept 2005

“I would say [Nicolette Sheridan is] in the 4 or 5 category… I like the way she used to look. I don’t like the way she looks today… I think she’s a solid 4… She went from being very flat chested. I feel like a person who’s flat chested is very hard to be a 10. I mean, there has to be extraordinary. You have to have the face of Vivien Leigh to be a 10 if you’re flat chested. Okay? But she went from an 8 to a solid 4…

“Yeah [Marcia Cross is a 3]. I hate to say it because I met all these people and they were so nice… Would you go out with Marcia Cross or would you turn gay, Howard? … She’s in that, she’s in the category. You know, solid 4 to 5…

“Gwen Stefani, I like. I mean she’s got great style. An 8…

“I know Paris Hilton off cam. I think Paris is a 9…

“I think Jessica Simpson is a good 8 or 9…

“No [Dakota Fanning will not ‘grow up hot’]. No. She will always be cute…She’ll never be hot…

“No [the Olson twins are not ‘hot at all’] now… And they never were.”
- Sept 22, 2005

“I don’t think [Angelina Jolie is] good looking at all… I’ll rate her a solid 5… Bad skin…

“I’d say [Jennifer Aniston is] a 6 or a 7…

“I think [Princess Diana] was great. I think she was — I mean other than she was wacky, I think that she was close with 10…

“I know women. Of course, I wouldn’t touch them because I’m a happily married man. But I know women…

“Everybody loves Ivanka… You know, you talk about a great beauty, but she’s a great beauty and everybody wants to go out with her. Every guy is calling her and I have to really guard her…

“See, I would only allow my daughter — see, I don’t want anybody to take after me. I want my daughter to be with somebody relatively her own age. I don’t want her to be like her father where I go out with girls where there’s a 24-year difference…

“She’s actually always been very voluptuous. She’s almost 6 feet tall… She’s been — you know she’s an amazing beauty…

“If I weren’t married, I’d be able to get all of the girls I want except for possibly Robin [Quivers]… Oh, absolutely. I’d have no trouble [‘banging 24-year-olds’]. I have no problem.”
- Oct 10, 2006

“Rosie O’Donnell’s disgusting. I mean, both inside and out. You take a look at her, she’s a slob. How does she even get on television?…

“If I were running The View, I’d fire Rosie. I’d look her right in that fat, ugly face of hers and say, ‘Rosie, you’re fired.’ We’re all a little chubby but Rosie’s just worse than most of us. But it’s not the chubbiness—Rosie is a very unattractive person, both inside and out. Rosie’s a person that’s very lucky to have her girlfriend and better be careful or I’ll send one of my friends over to pick up her girlfriend. Why would she stay with Rosie if she had another choice?

“Probably I’ll sue her…I’d like to take some money out of her fat-ass pockets.”
- Dec 21, 2006

“Rosie…is she a mess or what? You look at that slob. Is she a mess… Let me tell you, she’s a bad person. I know her. She’s a bad person… I go on The Today Show, Meredith Vieira, and she says, ‘Is it true that you called her crude?’ I said, ‘No. I called her a degenerate.’ She’s like ‘Okay. Did you call her fat? I said, let me ask you, ‘is she fat?’ ‘I’d rather not answer that question.’ … And you know, I’m very happy she’s fat… That is one of the most unattractive people. And you know, she took great offense at the fact that I said she better be careful or I or one of my friends will go and pick up her wife…

“You know, last week, before [Anna Nicole Smith] died, Entertainment Tonight was doing…a lot…on Anna, and I didn’t find it… I didn’t want to watch it. And I think it was the way she was talking. She was obviously drugged out. I don’t think that was even alcohol. I think that was drugs, but she was horrible.

“And it looked like she had the lips pumped. All of you many women listening, why do women have their lips pumped. I think it’s the most disgusting thing to look at these big, fat, pumped-up tires.”
- Feb 12, 2007

“And the girls — we’re supposed to call them women, but they’re girls to me — the girls, you can stay the entire speech… They want to torment me, and they always have beautiful women over here, and I’m sitting up making this speech, and I can’t stand it. Girls, get off this stage right now…

“[Rosie O’Donnell] announced last week that she suffers from depression… If she stopped looking in the mirror, I think she’d stop being so depressed…

“This slob, now I’m not allowed to use the word fat. They say, ‘he used the fat word.’ I know much worse words. It’s funny, I called her a degenerate, I called her the worst things, nobody cared. But I go on the Today Show and Meredith Vieira…said, ‘Is it true that you called Rosie crude?’ I said, ‘no, I called her a degenerate. I didn’t call her crude, it’s not strong enough.’ She goes, ‘But did you call her fat?’ I said, ‘Let me ask you a question Meredith. Is she fat?’ ‘I’d rather not comment.’ Can you believe this bullshit? This is politically correct bullshit, OK?”
- March 2007

“And I remember at the Academy Awards a few years ago she was frenching her brother. She was giving her brother lip kisses like I never saw before in my life. And she had just said she made love to Billy Bob Thornton in the back of the limousine on the way over. And I wouldn’t want to shake her hand, by the way…

“And now she’s like this great beauty who is representing world peace and the United Nations. It’s called give me a break. But she’s not — in terms of beauty, she’s not a great beauty She’s a nice looking woman. She’s OK. But she’s not a great beauty…

“I really understand beauty. And I will tell you, she’s not — I do own Miss Universe. I do own Miss USA. I mean I own a lot of different things. I do understand beauty, and she’s not.
- Oct 15, 2007

“You know I’ve always said Rosie’s a dummy. You know Rosie’s not smart… Rosie will always self-destruct, Howard. She’ll always self-destruct in the end she’s a loser…

“I think [a fight between us would] be close. She is pretty – You know, she ever fell in the wrong direction I wouldn’t have a chance… She came to my wedding… I got extremely angry because she ate almost the entire wedding cake… There was nothing left…

“I never thought [Angelina Jolie] was good looking. I don’t, I don’t think she’s got good skin. I don’t think she’s got a great face. I think her lips are too big to be honest with you. You know, they look like too big… And now they’re saying, she’s a lady of the, of the peace. She’s a — I mean give me a break. But I never thought she was good looking… I don’t think she is good looking at all… She’s a 7, but a 7 is not a 10…

“Ivanka is a 10…

“Let’s see — a 10. There are very few of them around… I think Paris is a good looking girl. Uhm, I mean there are you know, there are a lot of — 10s are very very hard to find…

“[When Britney Spears] was a virgin…she was so cute. And I remember I was in an audience at the Taj Mahal in Atlantic City, and she was performing and I was in the fourth row, and she was sweating and looked beautiful and she threw her hat, right? Now normally of a performer throws a hat and it’s sweaty and wet and everything, I’d have no interest in it. But I grab that sucker… I wasn’t even afraid of those germs. Today, if she threw it, I’d say ‘get that sucker out of here.’…

“[In my new show ‘Pageant Place’ the women] are seriously beautiful. [If any of them ‘show any signs of ugliness or aging’] they get terminated immediately.”
- Oct 10, 2007

“[Women ‘come up’ and ‘offer themselves to me] in levels of beauty that you wouldn’t believe. And they’re really, I mean, some incredible beautiful women that walk up and they’ll flip their top and they’ll flip the panties…

“I had sex with women that got fat. Many times…

“Isn’t it unbelievable, women are — one woman, beautiful, had big beautiful real boobs, really beautiful. And she wants them reduced… I think anybody is insane if a woman is… I have never seen a good breast reduction…

“Somebody said to me how did you make [the Miss USA pageant] so successful? I said, Number one, I got the best looking girls in the world. Number two they wear six-inch heels. And number three they were the tiniest suits you’re allowed on television…

“I go on The Today Show and Meredith…starts off, ‘Donald what about Rosie O’Donnell…do you hate her annd did you call her fat.’ I said, ‘No. I called her degenerate.’ I didn’t use the word fat because it’s politically incorrect but I did call her a total degenerate and I did call her a pig. I shouldn’t have called her that.”
- July 16, 2008

“At the Super Bowl, when Beyoncé was thrusting her hips forward in a very, very suggestive manner, if somebody else would have done that it would have been a national scandal. I thought it was ridiculous… I just thought it was not appropriate…

“I love [Halle Berry’s] upper body. I think her skin is beautiful. Yes I’ve seen her, you know many times. What I hate about Halle Berry, is that there’s always like, drama around her…

“Does [Kim Kardashian] have a good body? No. Does she have a fat ass? Absolutely. And if it weren’t Kim, they’d say, ‘Wow, I don’t want to go out with her.’…I don’t know [what the appeal is].”

“No [Mila Kunis is not ‘hot’], not to me. Not at all. She’s an attractive person. But when you look at Diana Mendoza, when you look at the Miss Universe people, you know, that’s why I’m so jaded…

“No [Jessica Chastain is] certainly not, she’s not hot.”
- Feb 6, 2013

“Jennifer Lawrence…has a little skin problem. I would say a little rough with her skin…

“Well, absolutely [Kim Kardashian’s ‘ass is too big’]. Of course. It’s record setting… In the old days, they’d say she’s got a bad body.”
- June 17, 2014

‘I know where [Hillary Clinton] went [the bathroom] — it’s disgusting, I don’t want to talk about it. No, it’s too disgusting. Don’t say it, it’s disgusting…

“She was going to beat Obama. She was going to beat – she was favored to win – and she got schlonged. She lost.”
- Dec 21, 2015

“She was the winner, and she gained a massive amount of weight, and it was a real problem. We had a real problem.”
- Sept 27, 2016

“Right now I am being viciously attacked with lies and smears. It’s a phony deal. I have no idea who these women [who are accusing me of sexual assault] are, have no idea. I have no idea…

“That horrible woman last night… Whoever she is, wherever she comes from, the stories are total fiction. They’re 100 percent made up, they never happened, they never would happen… These are lies being pushed by the media and the Clinton campaign to try and keep their grip on our country. They are all false, they’re totally invented, fiction. All 100 percent totally and completely fabricated. Never met this person, these people, I don’t know who they are…

“Some are doing it for probably a little fame, they get some free fame. It’s a total setup… One came out recently where I was sitting alone in some club. I really don’t sit alone that much.… It’s like unbelievable… “She’s a liar. She is a liar… These people are sick. These people are sick…

“I’m standing at my podium and [Hillary] walks in front of me, right? She walks in front of me, you know? And when she walked in front of me, believe me I wasn’t impressed…

“The only way they figure they can throw [my campaign] down is to come up with people that are willing to say, ‘I was with Donald Trump in 1980. I was sitting with him on an airplane, and he went after me on the plane.’ Yeah, I’m going to go after — Believe me, she would not be my first choice, that I can tell you. Man. You don’t know, that would not be my first choice.
- Oct 14, 2016

“Plus, she was very, very nasty to — one of the reasons it surprised me, she was very — she was probably nastier than even Pocahontas [Elizabeth Warren] to Joe Biden. She was very disrespectful to Joe Biden.”
- Aug 11, 2020