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No, seriously, Tiffany’s favorite place to unwind comes with both beautiful sweeping views of Los Angeles and a sprinkle of eye candy. I find this out when we meet for an early-morning hike—her suggestion, not mine.

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Certainly not the kind of setting where it would have occurred to me that my cover interview subject might flirt with someone(s), but here we are. You have to admire—and be unsurprised by—the confidence.

After all, this is the woman who, in the five years since her breakout performance in Girls Trip, has brought in somewhere in the neighborhood of a billion box-office dollars. From this summer’s Easter Sunday to her upcoming film Back on the Strip, she’s now a movie theater mainstay. Pick almost any streaming service and you’ll find more Tiffany projects—subscribe to Apple TV+? Check out her latest series The Afterparty. Looking to Netflix and chill? Try Black Mitzvah, Like a Boss, or Bad Trip. More of an HBO Max person? You’ll love The Card Counter. Hooked on Hulu? Binge The Carmichael Show. She is, quite literally, at the top of her game.

As it turns out, the trails we’re walking today were walked by a different Tiffany, years ago, who could only have imagined all this. She pauses to tell me: “When I was homeless, I used to come over here all the time and just dream.”


It’s a moment of unprompted vulnerability that I realize is kind of her thing. She’s not one to run from the hard parts of her story, from the childhood in foster care or the years of just barely getting by. At 42, Tiffany’s learned that if you pay attention, there’s wisdom to be found on the other side of trauma. And she’s learned just how important it is to give herself moments to breathe—whether that’s on her private island (yeah, read on) or right here in the park that has offered her comfort from the very beginning.

Michael Kors Collection blazer and dress. We Dream in Colour earrings.

[So, yes, we are hiking, and yes, I am puffing out these questions between gasps for air.] With everything you have going on, how do you set boundaries between work and self-care?

I love and hate telling people no. I love it because it’s for me—I have to take care of Tiffany. I hate it because nine times out of ten, whoever’s asking me is somebody I probably really like and care about. If a friend wants me to do a show or something like that, I have to be honest and say, “I can’t do it. I gotta get up early in the morning and the reason I gotta get up so early is because I need to go for a walk.” So you just got to be selfish in a way, and I hate that feeling of being selfish, but I love the results.


I know this is one of your favorite places to relax. But you’re also a Sagittarius, and I don’t know a Sag who doesn’t love to travel. What’s on deck when you can actually get away?

If I’m shooting a TV show and I only get two days off, I will rent a hotel somewhere like Marina del Rey or Malibu and take my surfboard with me and go out and pretend like I’m in Hawaii. And then when I have five days, I’ll be like, “I got to go, guys. Can’t do anything. I’m blocked.” I go to Eritrea often because I have land there, family there, and I love going there. I plan on going to Japan this year. Bermuda is, like, my favorite favorite. The people are nice; the food is good and doesn’t taste like it’s got GMOs in it. I’ll probably buy a house there and make it my vacation spot.

Missoni dress. Alexis Bittar cuff and lucite earrings. Jennifer Fisher gold earrings.

I loved learning that your father was Eritrean and watching you explore that culture. I’m first-gen too. My family is Kenyan and I remember how impactful my first few trips there were for me.

Every time I go, I feel like I grow as a person, my soul grows, and I know the country grows too. It’s a wonderful experience. It’s made up of hundreds of islands, and I have an island there. Now, granted, the ocean covers it for about four or five hours a day, but I got an island though. We could go there on the boat and hang out for about six, seven hours.

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We don’t talk enough about what a privilege it is to travel, how so many people never get to. Growing up, did you ever imagine yourself traveling at this level?

It was something I always dreamed about. My grandma used to have this abandoned, broken-down Chevy in the backyard and me, my cousins, and my sister used to pretend like we were driving to places like Chattanooga or Istanbul. But the car wasn’t a car. It was a magical train that could fly and we would go to all these cool places, and we get out and it’d be the same backyard. This is probably why my imagination is so great now. And I would say, “When we grow, we are going to do this for real.”

That’s really sweet. I don’t know about you, but I have broke PTSD. Do you struggle with that?

I got it too. So immediately when I started making a little bit of money doing things like Tyler Perry’s If Loving You Is Wrong and The Carmichael Show, I started trying to figure out how to create generational wealth. The fastest way to do it and the first way you should go about doing it is buy some land. So before we even got into season 2 of The Carmichael Show, I bought a house. Everybody told me I should wait, but I didn’t care. I just knew I was going to have to always make enough money to take care of me and the house, and that’s what I did. Between that show’s next season, the Keanu movie, and making sure I can live comfortably off of $500 a month, I was able to pay off half the house. The Girls Trip check was the final check. People told me to spend it in other ways, but I used it to pay off the house because I was always afraid of being homeless again. Now I have a surplus of money, but I’m still afraid of being poor again. Every movie I made, I would just buy another piece of land or a house.

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I’ve seen clips where you talk about buying and re-wearing dresses for awards shows because you want to get your money’s worth—are designers not offering to lend you clothes for events?

It’s a choice. I met Robert De Niro at the Laugh Factory in the lobby and he was talking about how in his contracts, it says that everything he wears, he has the option to keep.1 And then Beyoncé, everything she wears, she keeps in storage, she archives it.


So I said, “Well, that’s what I’m going to do. When I get a little bit of power, I’m going to archive it and I’m going to keep it.” At first, nobody wanted to dress me or lend me anything to wear. So I had to buy stuff. Then it got to the point where people are lending me stuff, but then I want to keep it because I like it and I want to wear it again! With a Dolce & Gabbana dress in particular, the plan was for me to buy it. But they said they had got so much press on it that they gifted it to me. Then I went to the store and ended up buying a bunch of other stuff. It’s an investment, right?

1. Robert De Niro had 102 clothing changes for The Irishman alone, and my mind is now spiraling wondering what he plans to do with it all.

Was there a specific moment when you realized or allowed yourself to accept that this is your life now?

I’m just getting to that. It is a huge struggle. I should have realized probably three years ago that I was, like, popping because people I know would be like, “You need to just put me in a movie. Give me the job. You got the power.” But I didn’t realize I had power. I didn’t understand it, and they knew before I knew. I just recently went to Harvard and took this class called The Business of Entertainment, Media, and Sports. I realized in that class that I’ve really been selling myself short all these years. You need the writer to tell the story, to put the story down on paper, but you need the performer to bring it to life. And the right performer puts the booties in the seats. You need the booty in the seat. You need eyes on the project, and the element that I was missing was that I had value in that way. It’s not about money. It’s about the power and then being able to create opportunities. Like on my show that I’m on right now, The Afterparty, I put in a request to see more people like me on the set.

Cult Gaia cover-up. Gold & Honey earrings. Jennifer Fisher rings.

I think a lot of people might be surprised to hear that was such a recent realization. How do you go about selecting which projects or partnerships you want to pursue?

I’ve turned down, shit, I’ve turned down $10 million just to do a post because it didn’t represent my brand. I turned down $10 million because my soul is worth more than that to me. My spirit, my integrity, how I want to be able to look at myself in the mirror every day…I’d rather be flat broke than get money to do something that makes me feel like shit.

At first with acting roles, I used to just be like, what seems like fun? Now it’s, what seems like fun and what resonates with my soul? Then I ask, who else is working on it? Will it be my friends? What I’ve noticed lately, though, is that casting has been coming to me first. So I’ve learned how to fight better too. Because it’s a battle getting the people that you want, because everybody still looks at you as talent, when they fail to realize I’ve produced things, got nominated for awards, won trophies…I kind of know what I’m doing. Give me an opportunity to make you richer, sir. I might not know how to keep a man, but I know how to make some money.

Missoni dress. Charlotte Stone sandals. Burberry sunglasses. Alexis Bittar cuff, ring, and lucite earrings. Jennifer Fisher gold earrings.

[As if on cue, a man walks by and starts to pass us.]

Tiffany: Damn, daddy, you’re fine as hell. Are we slowing you down?

Random Fine Hiker: What was that?

Tiffany: I said you’re fine as hell. Are you enjoying the view?

Random Fine Hiker: A little bit of both…can I get a picture?

Tiffany: You want a picture? What’s your baby mama gonna say?

Random Fine Hiker: I don’t have one…aren’t you an actor?

Tiffany: I’m an entertainer, darling. I don’t just act. I’m a creator.

[They take a picture and he goes on his way as Tiffany continues her commentary for me.]

Strong legs. You know, there’s a lot of real hoochie daddy shorts in Europe, you ever been? If you ever get a chance to go to Santorini, the men are beautiful. The food is delicious. I don’t care what hotel you’re at, you’re going to have a beautiful view. And the men walk around in them hoochie daddy shorts. It’s fun to watch. I like watching.

Versace top, bra, and skirt. Aquazzura sandals. Gold & Honey earrings. Jennifer Fisher cuffs and rings.

Is watching all you’re up for right now? Are you dating?

I’m queendom-building right now. But if some potential suitors show up and they want to take me somewhere….

Take you out on a date while you’re building the queendom. A little wine and dine.

Yeah. They might have some contribution. You know what I’m saying? I have been dating my ass off. That’s one thing that’s been really great. I know all the fine restaurants now. I got a date coming up where I’m dining in the dark. You order your food before you go in, and you go in and it’s dark, and the food is supposed to be really good because you can’t see.

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Do you have any dating advice?

Put on something cute but not too fancy. Be ready for if you go dancing, some shoes that are cute but comfy. I don’t want to be complaining. I’ll wait until date three or four to be that date. I’ll do something uncomfortable and see how he handles my discomfort because you need to know that before you lay down with a man, unless he’s going to be the jump-off.2 I’m hoping someone will earn their way into my bed soon. But I got the Rose3 off of Groupon, and that thing is amazing. And it travels well. Now, if you’re into penetration, all that stuff, it’s not going to really get that part, but that’s why I got a rose quartz penis off of AliExpress that’s amazing. I think it’s helping me heal.

2. A jump-off (n.) is a common phrase for a person you hook up with casually with no expectations of dating or commitment.

3. The Rose is one of the hottest vibrators on the market right now, as seen in many a Cosmo sex-toy roundup.

Wait. Like a crystal but shaped like a penis?

Yes, and it’s my favorite size too. I’ll put it outside in the moonlight to charge. Once, my sister came by and I forgot it was outside. She was like, “What the heck is that?” I was like, “Oh, give me that back!” I didn’t want my niece to see it.


Oh my god. You’re known for being outspoken, which comes with its pros and cons. How have you managed to stay true to yourself in an industry that tends to try to polish celebrities as they ascend?

Girl, they be trying to polish me. They be trying their best. I ain’t perfect. There is no way on God’s earth that I’m not going to make mistakes, that I’m not going to say something out of pocket, that I’m not going to be out of order. But I’m willing to learn and I’m willing to evolve, and how I feel today might be different than how I feel tomorrow. But if you don’t make mistakes, you’ll never grow. You’ll never be successful. Every successful person I know that’s winning has failed multiple times.

Et Ochs gown. Alexis Bittar earrings. Jennifer Fisher rings.

I often hear men talk about how it’s never been a harder time to be a comic. Do you agree?

No, I do not agree. I feel like it’s a harder time for men to be comics because a lot of them…hmm, how candid can I be? They become comedians so they can get laid. Now, you might get a charge pressed against you. And then they say, “You can’t say what you want to.” I think you can say what you want. It’s about how you go about things. Before, you could be reckless and try to figure it out. Now, you have to actually write and be clever and not come from a place of hate. I never thought you could just say horrible things about somebody and think they’re not going to slap the shit out of you, and I think that’s because I grew up in foster care. I check and verify with people. If I can’t say it to your face, I shouldn’t be able to say it. Period. That’s how I draw the line. I got this joke, “I curse you out with joy. I hope that you spread it. I hope you spread it like Usher spreads herpes.” I have said that in front of Usher.

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What’d he say?!

Usher said, “Your ass is crazy.” I said, “Yeah, well, there’s a rumor out there saying you got herpes. I don’t know if you do or don’t, but that shit is funny.” He’s like, “Yeah, it is.” If he had said, “Tiff, don’t say that no more. I don’t like it. I’m not comfortable with you saying that,” I would stop saying it.

I’m sure he appreciates that. Of all the things you do, is stand-up still your favorite?

It all leads to the stand-up. If you watch Black Mitzvah, you’ll see tears in my eyes because I tore my meniscus while shooting that thing. And I did not stop doing it, because I love it so much. To hear people laugh. It’s my drug. That’s my crack, baby.

We all could use more reasons to laugh right now, considering the bad news cycle we’ve been stuck in, from abortion rights being stripped away to the constant string of mass shootings to inflation. How do you manage to keep your joy when nothing feels funny?

I know that it’s going to be okay—whatever it is, it’s going to be okay. But I also know this: If they pass that law where they control our uteruses,4 I’m going to start getting into politics and I’m going to write a bill that makes it illegal for men to masturbate. Because every time you masturbate, sir, you ejaculate, sir, you’re killing somebody. That’s my opinion on that. But as far as joy, you gotta protect it. It’s not even just about protection. You got to manifest it. I also watch YouTube videos of babies laughing. That changes my whole vibe.

4. SCOTUS overturned Roe v. Wade shortly after this interview took place.


Sometimes you have to be proactive about it. For me, therapy plays a large part in that. I know you’re also active in therapy. What prompted that journey for you?

I was actually court-ordered to go to therapy as a teenager, but I didn’t really use it. I just was quiet, sitting there coloring, putting puzzles together, but I wouldn’t talk to the therapist. But when I was 21, I had a breakdown, so I went back and I really took it seriously because I felt like dying. It still makes me emotional when I think about it. I didn’t know why God put me on this planet to hurt so much? Why I had to be everybody’s punching bag. That’s where I let it sit. Right before I turned 18, I wanted to kill myself. My grandma told me I wasn’t allowed. She made me realize I was valuable. You know as a Black woman, we don’t talk about certain things like being molested or raped because we’re embarrassed or we think it will bring shame to the family or whatever. But I needed to talk about certain things. I think the biggest lesson for me is learning that it’s okay to say I’m not okay.

I feel that. As Black women, we’re often praised for being “resilient” and “strong,” but a lot of us weren’t taught how to tap into our vulnerability and softness.

This is the part I hate, and I don’t know if my phone has been listening to me or what, but I’ve been seeing a lot of posts about it on social media. I am not just a strong, Black woman. I am a woman. I need to be nurtured. I need to be protected. I need to be soft.

I think that’s why I love traveling so much. Something about the escapism and leisure of it all makes me feel like I can be my most relaxed and soft self.

Yes, I want to retire and buy a ranch in Wyoming. I will probably be traveling until the day I die, just going between all the properties in my queendom.

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Stylist: Wayman & Micah. Hair: Ray Christopher. Makeup: Hendra Nasril. Manicure: Yoko Sakakura using Dior Vernis. Executive producer: Abbey Adkison. Producer: Liesl Lar. Cinematographer: Janet Upadhye. Sound: Michael Rich. Editor: Heather Weyrick. Production: Wonder Partners.

On the cover: Cult Gaia cover-up. Gold & Honey earrings. Jennifer Fisher ring.

Headshot of Sylvia Obell
Sylvia Obell

Sylvia Obell is a writer and podcast host who lives in Los Angeles. Her work has appeared in New York magazine, Cosmopolitan, and Essence. Previously, she was an entertainment reporter for BuzzFeed News.