Right off the bat, let’s talk about that dress. Insecure creator and star Issa Rae came out for Wednesday’s Late Show in a striking, sherbet-orange X-front gown that the admiring Colbert yet noted was perhaps not the best choice for the freezing Ed Sullivan Theater. “I wasn’t gonna say anything,” admitted the nearly shivering Rae, telling Colbert that at least her custom Vera Wang wedding gown was a little warmer during her secret wedding to longtime boyfriend Louis Diame back in July. Of course, Saint-Jean-Cap-Ferrat, France in the summer is not New York in October, but Rae made the best of things on Wednesday, telling Colbert all she could about the upcoming fifth and final season of the series that launched her career.
“This was terrifying, you know?,” admitted Rae going into the last leg of her and her character’s journey. Noting that Insecure shares a network in HBO with another acclaimed series that, many might say (and have said) resolutely did not stick the landing, Rae told Colbert that the most common advice she gets on the street from Insecure fans is, “Girl, just don’t Game Of Thrones it.” Colbert employed a delivery room metaphor for Rae’s TV baby, suggesting that you don’t want to carry something precious for four years only to “drop it” at the worst possible time. Rae, instead, threw to Insecure writer and executive producer Amy Adiobe, who’s adopted more of a “landing the plane” mindset for Insecure’s ending.
“These characters aren’t going anywhere after this show,” said Rae, “They’re going to live on, so, it’s not that the plane is landing. They’re taking off and we’re just jumping out.” What, exactly, that means for Issa, Molly, Lawrence, and perpetual scene stealer Kelli (Natasha Rothwell), Rae’s not telling, although the clip she brought to The Late Show proves that Issa Dee’s habit of giving herself mirror pep talks continues right up ’til the end. (And that college-age Issa is adorable in braces and twists.) Colbert praised Rae for coming “out of the blocks” to score acclaim, Emmys, and a burgeoning media empire with her very first show, and Rae said that it’s, indeed, been an amazing five-year sprint to this particular finish line.
“You know, I was, for lack of a better word, insecure,” said Rae, telling Colbert that all of the success and support she’s received (and earned, one might add) in that time has led her from “insecure” to “capable.” And while Rae noted that she’s not gunning for Oprah’s spot in the media landscape just yet, she’s pretty sure that she can take down Gwyneth Paltrow before too long. (Rae might not be hawking $35,000 pyramid commodes, but she is co-owner of eco-friendly hair care company Sienna Naturals, along with production company HOORAE Media.) Telling Colbert about her fondness for kicking back and enjoying her success via the occasional karaoke yacht party, Rae deftly invited Colbert along for her next aquatic get-together, perhaps having seen how readily Colbert will glom onto his guests’ private functions. No matter, as Colbert, bewildering Rae with some suitably old-timey dad joke terminology (he promises to break out the “old Jack Johnson” when it comes to karaoke), seems certain to bring the aging white guy energy to the party, along with his boat shoes.
The fifth and final season of Insecure premieres on HBO this Sunday.