It wasn't that long ago that Issa Rae couldn't afford HBO. Now she's about to launch the second season of her critically acclaimed series "Insecure" on the premium cable network.
The L.A. native, who bypassed the conventional Hollywood system in launching her career, is part of a generation that's offering a fresh perspective on the complexity of coming into your own, with all its thrills and heartaches.
The first season of the the series, which she created, executive produces and stars in, drew praise for its portrait of that restless stage of thirtysomething-dom when work, love and friendship don't seem to be measuring up.
And Rae has been working hard to make sure Season 2 doesn't slip.
The grind began last November at the W Hotel in West L.A., where ideas flowed alongside mimosas — sometimes poolside — as she and show-runner Prentice Penny mapped out where they wanted to take the show next.
The debut season ended with some growing pains. The wreckage from the broken relationship between Issa Dee (Rae) and Lawrence (Jay Ellis) remained messy with the last moments of the finale revealing Lawrence having revenge sex with bank teller Tasha (Dominique Perry); meanwhile, the friendship between Issa and her bestie Molly (Yvonne Orji) had weathered the storm of unpleasant truths.
"What excited me about the characters is that everybody's worlds were turned upside down, and the rebuilding wasn't going as planned," Rae, 32, said during a recent sit-down.
Rae recalled knowing two things for sure going into that Season 2 brainstorming session:
1) She wanted Issa to go through what she calls the "ho phase," dating and sleeping with guys without inhibition. "It was something I really wanted to explore with Issa, the character. It was something that I missed out on in a way. And it feels like once you're past a certain age, it's frowned upon, like, 'girl, you're too grown to do that.'"
2) She wanted Lawrence to still be involved with Tasha.
Penny offers this insight on Season 2: "Issa and I think of it this way: Remember — or imagine — what happens when you have broken up after so many years with somebody and you're hit with realities you're maybe not ready to face. That's what you're going to see on this show. Overall, we liked this theme of the face you present publicly versus what you're going through behind closed doors."
Beginning Sunday, viewers will see those faces when the sophomore season premieres. And there could be more eyeballs this time around. In a vote of confidence, HBO moved up the premiere date so it could place "Insecure" in a plum spot behind the network's ratings powerhouse, "Game of Thrones."
"For us it was like 'Yeah, baby!'" Penny said of the new time slot. Rae described it as "so freaking cool."
Cool, sure. But not without some repercussions.
The writers room opened up just after Thanksgiving 2016 to begin work on the 10 episodes ordered for Season 2. The assumption was the show would again have a fall rollout. But a couple of weeks in, word came from HBO brass of the interest in bumping up the show's premiere date. Not wanting to pass up the opportunity Rae and Penny decided to trim the episode count to eight.
"Because it's the second season, you don't ever want anybody to be like, 'You could tell they rushed it' or 'It's not as good as Season 1,'" Rae said. "We had lots of discussion about whether or not to accept HBO's offer."
"We were like, 'But it's 'Game of Thrones'!" she continued, remembering the animated debate, "but we were also like, 'The time! And we want it to be good! Will we be too rushed?' Eight episodes seemed to make everyone happy. But it was definitely a constant scramble. I would rest between takes."
That reality seemed to be on display during a visit to the show's set on the Sony Pictures lot in Culver City.
In May, filming on one of the later episodes of the season took place with a scene in Issa's apartment. The character was supposed to be startled awake by her alarm and leave in a mad dash. As the director yelled "action," a voice off screen stood in for the sound of the phone: buzz, buzz, buzz, the voice said.
Long silence. … No mad dash.
"Wake up, bitch!" executive producer Melina Matsoukas jokingly yelled from behind monitors.
"You said four buzzes!" Rae shouted back, amused.
"She wasn't getting up so I thought she was really sleeping again," Matsoukas mumbled with a laugh to those around her.
Rae's goal for Season 2 was to stay authentic, but for the characters to be a bit more bold. Even the title scheme builds on the concept of raising the stakes — the season premiere is titled "Hella Great," Episode 2 is "Hella Questions."
Rae and her producers also knew that, with the foundation now in place, they wanted to elevate the look of the series.
"I wanted it to feel as filmic and cinematic as possible without losing that real feel," said Matsoukas, who also directs on the series and is known for her music video work with Rihanna and Beyoncé.
Matsoukas said attention was paid to visually express the dimness of some of what the characters are experiencing — making use of mixed lighting and letting some scenes hang in the shadows.
"I want to tell a real story," Rae said. "And I want it to also look and feel real."
The vein of authenticity is important to Rae and speaks to her roots in the DIY world of YouTube.
Before the writer-actress was exploring the themes of race and identity on "Insecure," she tackled them on the Internet — most notably through her Web series "The Misadventures of Awkward Black Girl." That she was able to parlay "Black Girl" into an HBO series that has struck a chord with viewers — including former President Barack Obama — keeps her motivated.
"Just being able to have a TV show, on the air, on a premium cable network — a show that I am proud of is something that I don't take for granted," Rae said. "And knowing that this came from, in its earliest stage, a YouTube video that I posted in 2007, on a whim, that trips me out in the best possible way."
And as a black woman in Hollywood, the significance of that is not lost on her.
"I've watched the tides change," Rae said. "I've watched people not be interested in anything black women have to say or be interested in a specific thing black women have to say to 'Oh, black women are everything, pitch us ideas! We're interested now. 'Scandal' worked — what else is there?'
"And I know the struggle," she continued, "of having your first show and wondering if it will still be your voice and wondering, if you put your foot down, will you lose an opportunity not only for yourself but for your peers who are trying to break through? I get it. But our time is coming."
And the online world remains an integral component of her career and her desire to do her part to help expand the spotlight on minority voices. She's coy about her latest, rumored project, which originally started as an Internet meme. A photo of Grammy winner Rihanna with Oscar winner Lupita Nyong'o taken in 2014 at a Miu Miu fashion show went viral earlier this year, prompting calls to turn it into a buddy movie. Twitter users suggested Ava DuVernay as the director and Rae as the screenwriter. It wasn't long before Netflix reportedly hammered out a deal to make it a reality.
"I owe the Internet my entire career, I wouldn't be here today without it," Rae said, dancing around the status of the project. "Just the fact that someone nominated me to even be a part of the project, then people co-signed — it was incredible."
In tribute to her online roots and loyal following, HBO is making the first season of "Insecure" available for free on its YouTube channel — as well as HBO.com — for 24 hours starting at 3 a.m. PT on Sunday.
"I've had people come up to me so many times saying, 'I wish I could watch your show but I don't have HBO, I can't afford it," Rae said. "I tell them straight up, 'I didn't have HBO either. I get it. I mean, I was using my friend's password until I got the show.' Then I was like, 'OK, I guess I'll pay.' So I get it. And I'm glad it's now accessible to more people."
And not only can Rae afford HBO these days, she's finally getting around to commemorating this chapter in her life with a yacht party this weekend.
"I've been trying to do yacht stuff this summer to feel like a high roller," she said. "Whether I document on social media will depend on my level of inebriation and seasickness."