Issa Rae covers Vanity Fair's June issue looking ready for business in a crisp black suit offset by a gold, armor-like bustier that levels up the whole ensemble. In fact, "Issa Rae Levels Up" is emblazoned across her image and the cover story inside is fitting of the headline. Not only is the writer/actor/producer gearing up for the final season of her "baby" Insecure, but she's hitting the ground running with several projects in the works.
Issa's lineup includes producing a Baldwin Hills-esque docu-series Sweet Life and an adaptation of popular podcast Nice White Parents, plus she's writing, producing, and starring in Perfect Strangers. She also has a second season of A Black Lady Sketch Show which she executive produces coming up, and she's working on a revival of Matt Damon and Ben Affleck's HBO docu-series Project Greenlight, which gave money and support to aspiring filmmakers. So yeah, "levels up" is probably an understatement for what the 36-year-old has coming.
With all these new endeavors happening, one thing remains prevalent throughout Issa's work—the range of relatable Black women characters. If you're an Insecure fan, you know exactly what I'm talking about. Each season the women only get more complex and the introduction of new female roles only adds layers. Her mission is to do this for Black woman characters across the scope of her work.
In her interview with VF, she shares an interesting anecdote of hurting Lauren London's feelings a few years ago that really drove this message home. Luckily, the two have made up since—in part thanks to the late Nipsey Hussle for encouraging Issa to defuse the situation at a birthday party for Diddy.
Rich Polk/Getty Images for ESSENCE
Issa recalls a previous interview she did where she told the story of a TV executive who suggested that Lauren, most known for roles in ATL and The Game reboot, play the lead for a cable version of her YouTube hit Awkward Black Girl. That show became what we all love and know today as Insecure, which we can't imagine anyone else other than Issa as the off-beat leading lady.
And Issa couldn't imagine Lauren encapsulating the awkwardness that her character Issa Dee (based on her real self) embodies. Her point was that executives were out of touch with Black women and thought of swapping one for another even when they were nothing alike, but also that dark-skinned Black women could be edited out of their own narratives.
However, Issa's comments in the interview hurt London's feelings.
"One of my biggest regrets, naming her. She took offense to that."
It wasn't until the aforementioned Diddy birthday party two years ago where the pair reconciled:
"[Nipsey] was like, 'You should just talk to her. Let me set it up.' It actually sparked an amazing two-hour conversation. We had so much in common. She was like, 'People don't understand, I'm an awkward Black girl.' In the same way that I was upset about the limited portrayal of Black women, she was like, 'People do the same thing to me.' I completely get that."
Consider the situation a lesson learned. Issa continues to expand her concept of Black female characters.
She also admits to still being in a group chat with Rihanna, Lupita Nyong'o, and Ava DuVernay ever since a rival photo from NYFW '16 that Twitter wants made into a movie, and we concur.
The more versatile Black woman roles, the better.
Featured image by Rich Polk/Getty Images for ESSENCE
Amber Riley has the type of laugh that sticks with you long after the raspy, rhythmic sounds have ceased. It punctuates her sentences sometimes, whether she’s giving a chuckle to denote the serious nature of something she just said or throwing her head back in rip-roarious laughter after a joke. She laughs as if she understands the fragility of each minute. She chooses laughter often with the understanding that future joy is not guaranteed.
Credit: Ally Green
The sound of her laughter is rivaled only by her singing voice, an emblem of the past and the future resilience of Black women stretched over a few octaves. On Fox’s Glee, her character Mercedes Jones was portrayed, perhaps unfairly, as the vocal duel to Rachel Berry (Lea Michele), offering rough, full-throated belts behind her co-star’s smooth, pristine vocals. Riley’s always been more than the singer who could deliver a finishing note, though.
Portraying Effie White, she displayed the dynamic emotions of a song such as “And I'm Telling You I'm Not Going” in Dreamgirls on London’s West End without buckling under the historic weight of her predecessors. With her instrument, John Mayer’s “Gravity” became a religious experience, a belted hymnal full of growls and churchy riffs. In her voice, Nicole Scherzinger once said she heard “the power of God.”
Credit: Ally Green
Riley’s voice has been a staple throughout pop culture for nearly 15 years now. Her tone has become so distinguishable that most viewers of Fox’s The Masked Singer recognized the multihyphenate even before it was revealed that she was Harp, the competition-winning, gold-masked figure with an actual harp strapped to her back.
Still, it wasn’t until recently that Riley began to feel like she’d found her voice. This sounds unbelievable. But she’s not referring to the one she uses on stage. She’s referencing the voice that speaks to who she is at her core. “Therapy kind of gave me the training to speak my mind,” the 37-year-old says. “It’s not something we’re taught, especially as Black women. I got so comfortable in [doing so], and I really want other people, especially Black women, to get more comfortable in that space.”
“Therapy kind of gave me the training to speak my mind. It’s not something we’re taught, especially as Black women."
If you ask Riley’s manager, Myisha Brooks, she’ll tell you the foundation of who the multihyphenate is hasn’t changed much since she was a kid growing up in Compton. “She is who she is from when I met her back when she was singing in the front of the church to back when she landed major roles in film and TV,” Brooks says. Time has allowed Riley to grow more comfortable, giving fans a more intimate glimpse into her life, including her mental health journey and the ins and outs of show business.
The actress/singer has been in therapy since 2019, although she suffered from depression and anxiety way before that. In a recent interview with Jason Lee, she recalls having suicidal ideation as a kid. By the time she started seeing a psychologist and taking antidepressants in her thirties, her body had become jittery, a physical reminder of the trauma stacked high inside her. “I was shaking in [my therapist’s] office,” she tells xoNecole. “My fight or flight was on such a high level. I was constantly in survival mode. My heart was beating fast all the time. All I did was sweat.”
There wasn’t just childhood trauma to account for. After auditioning for American Idol and being turned away by producers, Riley began working for Ikea and nearly missed her Glee audition because her car broke down on the highway while en route. Thankfully, Riley had been cast to play Mercedes Jones. American Idol had temporarily convinced her she wasn’t cut out for the entertainment industry, but this was validation that she was right where she belonged. Glee launched in 2009 with the promise of becoming Riley’s big break.
In some ways, it was. The show introduced Riley to millions of fans and catapulted her into major Hollywood circles. But in other ways, it became a reminder of the types of roles Black women, especially those who are plus-sized, are relegated to. Behind the scenes, Riley says she fought for her character "to have a voice" but eventually realized her efforts were useless. "It finally got to a point where I was like, this is not my moment. I'm not who they're choosing, and this is just going to have to be a job for me for now," she says. "And, that's okay because it pays my bills, I still get to be on television, I'm doing more than any other Black plus-sized women that I'm seeing right now on screen."
The actress can recognize now that she was navigating issues associated with trauma and low self-esteem at the time. She now knows that she's long had anxiety and depression and can recognize the ways in which she was triggered by how the cult-like following of the show conflicted with her individual, isolated experiences behind the scenes. But she was in her early '20s back then. She didn't yet have the language or the tools to process how she was feeling.
Riley says she eventually sought out medical intervention. "When you're in Hollywood, and you go to a doctor, they give you pills," she says, sharing a part of her story that she'd never revealed publicly before now. "[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that's not fixing my problem. If anything, it's making it worse."
“[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that’s not fixing my problem. If anything it’s making it worse.”
Credit: Ally Green
At one point, while in her dressing room on set, she rested her arm on a curling iron without realizing it. It wasn't until her makeup artist alerted her that she even realized her skin was burning. Once she noticed, she says she was "so zonked out on pills" that she barely reacted. Speaking today, she holds up her arm and motions towards a scar that remains from the incident. She sought help for her reliance on the pills, but it would still be years before she finally attended therapy.
This stress was only compounded by the trauma of growing up in poverty and the realities of being a "contract worker." "Imagine going from literally one week having to borrow a car to get to set to the next week being on a private jet to New York City," she says. After Glee ended, so did the rides on private planes. The fury of opportunities she expected to follow her appearance on the show failed to materialize. She wasn't even 30 yet, and she was already forced to consider if she'd hit her career peak.
. . .
We’re only four minutes into our Zoom call before Riley delivers her new adage to me. “My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway,” she says.
On this Thursday afternoon in April, the LA-based entertainer is seated inside her closet/dressing room wearing a cerulean blue tank top with matching shorts and eating hot wings. This current phase of healing hinges on balance. It’s about having discipline and consistency, but not at the risk of inflexibility. She was planning to head to the gym, for instance, but she’s still tired from the “exhausting” day before. Instead, she’s spent her day receiving a massage, eating some chicken wings, and planning to spend quality time with friends. “I’m not going to beat myself up for it. I’m not going to talk down to myself. I’m going to eat my chicken wings, and then tomorrow I’m [back] in the gym,” she says.
“My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway."
This is the balance with which she's been approaching much of her life these days. It's why she's worried less about whether or not people see her as someone who is humble. She'd rather be respected. "I think you should be a person that's easy to work with, but in the moments where I have to ruffle feathers and make waves, I'm not shying away from that anymore. You can do it in love, you don't have to be nasty about it, but I had to finally be comfortable with the fact that setting boundaries around my life – in whatever aspect, whether that's personal or business – people are not going to like it. Some people are not going to have nice things to say about you, and you gotta be okay with it," she says.
When Amber talks about the constant humbling of Black women in Hollywood, I think of the entertainers before her who have suffered from this. The brilliant, consistent, overqualified Black women who have spoken of having to fight for opportunities and fair pay. Aretha Franklin. Viola Davis. Tracee Ellis Ross. There's a long list of stars whose success hasn't mirrored their experiences behind the scenes.
Credit: Ally Green
If Black women outside of Hollywood are struggling to decrease the pay gap, so, too, are their wealthier, more famous peers.
Riley says there’s been progress in recent years, but only in small ways and for a limited group of people. “This business is exhausting. The goalpost is constantly moving, and sometimes it’s unfair,” she says. But, I have to say it’s the love that keeps you going.”
“There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman,” she continues. “We’re still niche. We’re still not main characters.”
"There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman. We’re still niche. We’re still not main characters.”
Last year, Riley starred alongside Raven Goodwin in the Lifetime thriller Single Black Female (a modern, diversified take on 1992’s Single White Female). It was more than a leading role for the actress, it also served as proof that someone who looks like her can front a successful project without it hinging on her identity. It showcased that the characters she portrays don’t “have to be about being a big girl. It can just be a regular story.”
Riley sees her work in music as an extension of her efforts to push past the rigid stereotypes in entertainment. Take her appearance on The Masked Singer, for instance. Riley said she decided to perform Mayer’s “Gravity” after being told she couldn’t sing it years earlier. “I wanted to do ‘Gravity’ on Glee. [I] was told no, because that’s not a song that Mercedes would do,” she says. “That was a full circle moment for me, doing that on that show and to hear what it is they had to say.”
As Scherzinger praised the “anointed” performance, a masked Riley began to cry, her chest heaving as she stood on stage, her eyes shielded from view. “You have to understand, I have really big names – casting directors, producers, show creators – that constantly tell me ‘I’m such a big fan. Your talent is unmatched.’ Hire me, then,” she says, reflecting on the moment.
Recently, she’s been in the studio working on original music, the follow-up to her independently-released debut EP, 2020’s Riley. The sequel to songs such as the anthemic “Big Girl Energy” and the reflective ballad “A Moment” on Riley, this new project hones in on the singer’s R&B roots with sensual grooves such as the tentatively titled “All Night.” “You said I wasn’t shit, turns out that I’m the shit. Then you called me a bitch, turns out that I’m that bitch. You said no one would want me, well you should call your homies,” she sings on the tentatively titled “Lately,” a cut about reflecting on a past relationship. From the forthcoming project, xoNecole received five potential tracks. Fans likely already know the strengths and contours of Riley’s vocals, but these new songs are her strongest, most confident offerings as an artist.
“I am so much more comfortable as a writer, and I know who I am as an artist now. I’m evolving as a human being, in general, so I’m way more vulnerable in my music. I’m way more willing to talk about whatever is on my mind. I don’t stop myself from saying what it is I want to say,” she says.
Credit: Ally Green
“Every era and alliteration of Amber, the baseline is ‘Big Girl Energy.’ That’s the name of her company,” her manager Brooks says, referencing the imprint through which Riley releases her music after getting out of a label deal several years ago. “It’s just what she stands for. She’s not just talking about size, it’s in all things. Whether it’s putting your big girl pants on and having to face a boardroom full of executives or sell yourself in front of a casting agent. It’s her trying to achieve the things she wants to do in life.”
Riley says she has big dreams beyond releasing this new music, too. She’d love to star in a rom-com with Winston Duke. She hasn't starred in a biopic yet, but she’d revel in the opportunity to portray Rosetta Tharpe on screen. She’s determined that her previous setbacks won’t stop her from dreaming big.
“I think one of my superpowers is resilience because, at the end of the day, I’m going to kick, scream, cry, cuss, be mad and disappointed, but I’m going to get up and risk having to deal with it all again. It’s worth it for the happy moments,” she says.
If Riley seems more comfortable and confident professionally, it’s because of the work she’s been doing in her personal life.
She’d previously spoken to xoNecole about becoming engaged to a man she discovered in a post on the site, but she called things off last year. For Valentine’s Day, she revealed her new boyfriend publicly. “I decided to post him on Valentine’s Day, partially because I was in the dog house. I got in trouble with him,” she says, half-joking before turning serious. “The breakup was never going to stop me from finding love. Or at least trying. I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness, and you enjoy it and work through it.”
Credit: Ally Green
"I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness and you enjoy it and work through it.”
With her ex, Riley was pretty outspoken about her relationship, even appearing in content for Netflix with him. This time around is different. She’s not hiding her boyfriend of eight months, but she’s more protective of him, especially because he’s a father and isn’t interested in becoming a public figure.
She’s traveling more, too. It’s a deliberate effort on her part to enjoy her money and reject the trauma she’s developed after experiencing poverty in her childhood. “I live in constant fear of being broke. I don’t think you ever don’t remember that trauma or move past that. Now I travel and I’m like, listen, if it goes, it goes. I’m not saying [to] be reckless, but I deserve to enjoy my hard work.”
After everything she’s been through, she certainly deserves to finally let loose a bit. “I have to have a life to live,” she says. “I’ve got to have a life worth fighting for.”
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Take orgasms, for example. Since I’m well aware of the fact that vaginal orgasms (especially) can be a real challenge for a lot of women, I’m constantly on the hunt for what can help to “bridge the gap” in that arena.
And that’s why I decided, this time, to forego science articles, vlogs, and online data and instead ask some women for myself about some of the things that they do to make having an orgasm, improving their orgasms, and their sexual experience overall something that is so much better for themselves.
So, grab yourself a light aphrodisiac snack (check out “Eat Your Way To Better Sex With Aphrodisiacs”) and dig into what 15 Black women told me gets them off, in a mighty big way, just about every time.
*As always, middle names have been used so that everyone can feel comfortable giving up the goods…umm, so to speak*
1. Rochelle. 37. Married for 11 Years.
Giphy“While y’all be out here talking about some kegels, what I’m into is my man giving me a hip massage. The key is to make sure you use some sort of massage oil that has menthol in it. Between the tingling of the menthol and him rubbing on your hips, not only is it really relaxing, but the ‘minty feel’ opens your body up so that once intercourse begins, you’re less tense, and that makes having an orgasm so much easier to do.”
2. Karmyn. 27. Single.
“Kiss him the way you want him to penetrate you. Literally, use your tongue as if it were a penis and move it in his mouth like you want him to move inside of you. The kissing will turn you both on, and if he follows your instructions, you should be able to orgasm with no problem."
"I learned this trick when I asked an ex of mine to explain what p — sy feels like, and he said the best way to explain it is what a tongue feels like inside of [the] mouth. He should’ve never told me that, boy! It’s been hell in these streets ever since!”
3. LaChelle. 43. In a Serious Relationship for Two Years.
“If you’re self-conscious about your body, get some lingerie that has cutouts in them. There is a lot of sexy stuff out here that can have you covering up the parts you’re not comfortable with while still giving him access to the ‘main events.’ My man loves one of my lace one-piece teddies that has no crotch, and it’s easier for me to orgasm because I’m not overthinking the entire time.”
4. Trinitee. 27. Married for One Year.
Giphy“We’ve only been married a year, but we weren’t exactly abstinent when we were just dating. So, we like to find ways to keep it fresh. One thing that we do is go ‘hotel hopping’ once a month. We find a new hotel and meet each other there. We try and do different hours of the day and come with a surprise in hand. Like he might bring a new sex toy, and I might have on some lingerie that he’s never seen before. Then we text each other beforehand to talk about the best part of the sex we had from the last hotel we visited. The anticipation is foreplay.”
5. Wren. 33. In a Serious Relationship for Six Years.
“What works for me is doing afterplay as foreplay. What I mean by that is, taking a nap naked with my boo before any sexual activity is one of my favorite things. Being up under him, especially if he’s spooning me, feels really good, sleeping together is very intimate, and — there’s something about being awakened outta my sleep with kisses on my neck and back that almost makes me want to cum right then and there.”
6. Bevalyn. 40. Living with Her Partner for Four Years.
“Get on your back and have him kneel in front of you."
"Put your legs over his, and when he penetrates you, ask him to use one of his hands to apply pressure on your pubic bone — the area right above your clitoris."
"As he’s gently pushing down while he’s inside of you…if you don’t cum from that, I don’t know what else to tell you, sis.”
7. Sophia. 38. In a Serious Relationship for Two Years.
Giphy“Shower sex can be a bit much, and I don’t trust a used jacuzzi. What we do is fill up our own inflatable pool and get it on inside of it. It’s perfect during the summer, late at night, because we have a tall fence. Just make sure that you bring some silicone lube to keep things slippery down there. An inflatable pool has been one of the best sex investments that we have ever made!”
8. Averie. 35. Single.
“Wanna know if your man is as into giving you head as he claims? Right after he goes down on you, ask him to immediately penetrate you. If he’s hard, he’s totally into it, and if he catches you soon enough, you’ll be in the perfect position to have a multiple orgasm. Don’t say I didn’t give you the ultimate cheat code.”
9. Victoria. 40. Married for 11 Years.
“Shellie, you actually got me on the cinnamon kick when I read one of your articles that talked about applying cinnamon oil to my clit before oral sex. Since [then], I’ve been doing some research, and it says that cinnamon is also an aphrodisiac because it stimulates blood flow. So, I’ll also drink cinnamon tea throughout the day or share a cinnamon cocktail with my husband. Works like a charm.”
Shellie here: She’s right. I did say that. LOL. You can read for yourself: “Here's How To Have Some Really Great Fall-Themed Sex.”
10. Daniela. 28. Engaged for Six Months.
Giphy“Ever been fingered backward? What I mean is, get on all fours and have him insert a finger or two from behind with his palm being flat. That way, the space in between your anus and your vagina will get a massage while your vagina gets penetrated. There’s nothing quite like it.”
11. Saven. 32. Single.
“Ice. Have him rub a little bit of ice on your clitoris and then immediately warm it up with his tongue. There is something about the drastic changes in temperature that gets me every time. And I mean, EVERY time.”
12. Ferynn. 30. Living with Her Partner for Five Years.
“I don’t know about you, but my man loves to put my legs up in the air. It was never really my favorite move until I read that behind the knees are an unsung erogenous zone. Whoever found that out was onto something because if he rubs back there while talking real crazy to me in a deep voice? Here I come…HERE I COME!”
13. Vivienne. 30. Engaged for One Year.
Giphy“Never underestimate the power of a foot massage. Just make sure that he applies pressure in the middle of your foot where your arch is. It instantly makes me wet. I asked my doctor why and he said that it’s probably because foot massages tend to increase blood flow, including where the vagina is. Either way, it’s always a good night if I get a foot massage first.”
14. Michelle. 24. Single.
“I’m a doula who owns my own exercise ball…for sex. When I first started showing couples the positions that women can get into to make labor easier, it got me to thinking that some of those positions could work for sex too — and they do."
"Something about the movement of the ball takes the pressure off of the back for both men and women. It also makes getting into certain positions a lot easier so that you can enjoy sex for a lot longer.”
15. Carol. 31. Married for Five Years.
“My husband and I have bets. If he wants me to make some of his favorite meals five days in a row, he’s gotta make me cum five times in a row. If I want him to get me something that’s not in our budget, I’ve gotta attempt one of his sex fantasies. We’re both competitive as hell, so it works for us because honestly, even when we ‘lose’…we win!”
_____
Listen, I don’t know about y’all, but this was definitely worth my while. After all, ain’t nothin’ like some Black women who can speak from very-personal-and-up-close experience about what makes them happy — especially if it can increase the odds of bringing some sexual satisfaction your way too.
Speaking of, if you want to share the wealth, drop some of your own orgasm-related tips in the comment section. The more of us who can woosah on the regular, the better, chile. Straight up. #havefun #lotsofit
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