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Issa Rae Breaking News, Photos, and Videos

Issa Rae Cozies Up to Kendrick Sampson While Filming Fifth & Final Season of 'Insecure'

Filming for Insecure is officially underway!

Issa Rae and Kendrick Sampson filmed a scene on a city bench on Wednesday afternoon (February 10) in Los Angeles.

PHOTOS: Check out the latest pics of Issa Rae

The 36-year-old actress looked pretty in an all tan outfit while the 32-year-old actor sported a gray jacket and maroon basketball shorts for their scene.

Kendrick wrapped his arms around Issa while she rested her head up against his as they shared a laugh while filming.

Issa took to Instagram a few weeks ago to mark the first day of filming the fifth season Insecure.

“First Day of Season Bye-ve #InsecureHBO,” Issa wrote while posing outside of her trailer.

Issa announced last month that the upcoming fifth season of Insecure would be its last.

The final season of Insecure is expected to premiere later this year.

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'Insecure' Is Coming to an End at HBO With Season 5

Insecure is coming to an end.

The Issa Rae-helmed acclaimed HBO series will end with its upcoming fifth season, the network confirmed Wednesday (January 13).

Issa Rae

Prentice [Penny] and I are so grateful that HBO believed in our show from the beginning and kept faith in us to see our vision through the end. We always planned to tell this story through five seasons, but we couldn’t have made it this far without the tremendous support of our audience,” Issa told Deadline.

“I feel blessed beyond measure to bring our characters’ stories to an end, on-screen at least.”

The fifth season is expected to go into production later this month, and will star Issa, Yvonne Orji, Jay Ellis, Natasha Rothwell, Amanda Seales and Alexander Hodge. It will arrive sometime later in 2021.

The show was based on Issa’s online series Awkward Black Girl, and followed her as she navigated love, life and friendship.

There have been a lot of shows cancelled throughout the entirety of 2020 and Netflix especially has been cancelling left and right. Find out which shows have been recently cancelled by Netflix in the past few months.

Kanye West Reacts to Issa Rae Including Him in 'SNL' Joke

Kanye West is “praying” for Issa Rae.

The Ye rapper reacted to the Insecure star’s joke on Saturday Night Live in a tweet on Sunday (October 18).

PHOTOS: Check out the latest pics of Kanye West

“Ive always said SNL uses black people to hold other black people back. My heart goes out to Issa Rae. I’m praying for her and her family,” he wrote.

“I know that the twenty years of service that I’ve paid in the entertainment field has furthered our ability to be more successful.”

On SNL, Kanye was mentioned during the “Your Vote Chicago” speech, when Issa’s character appeared on a morning talk show to say she’s voting for “everybody Black” – except Kanye.

“When we come back, we’ll talk about the presidential race between Donald Trump, Joe Biden, and Kanye West,” Kenan Thompson‘s anchor character said, to which she said: “Kanye? F him!”

Issa Rae Talks Premiering 'Insecure' During 2016 Presidential Election in 'SNL' Monologue - Watch!

Issa Rae is hosting Saturday Night Live for the first time ever!

The 35-year-old entertainer hosted the hit sketch show on Saturday (October 17).

During her opening monologue, Issa talked about feeling “awkward” about premiering her HBO series Insecure back in fall of 2016 right after Donald Trump won the presidential election.

“The results came in, and, of course, everybody was freaking out. I was freaking out,” Issa shared. “And it felt really awkward for my life to be going so good. Like, it was rude to be peaking right when democracy was collapsing. It’s just really weird to say thank god for what happened in the fall of 2016.”

Check out Issa Rae‘s full opening monologue now!

'SNL' Announces Hosts & Musical Guests for Two More October Episodes!

NBC has announced the hosts and musical guests for two more episodes of Saturday Night Live, which will air in October 2020.

The season premiere of the Emmy Award-winning sketch comedy series is happening this weekend with Chris Rock and musical guest Megan Thee Stallion.

On October 10, comedian and podcast Bill Burr will be making his SNL debut as the host with country singer Morgan Wallen as the musical guest.

Issa Rae will be making her SNL debut when she hosts the October 17 episode with Justin Bieber as the musical guest, marking his fourth appearance on the show.

Saturday Night Live will continue to air live on both coasts this season.

ARE YOU EXCITED for the upcoming episodes of SNL that are on the way in October?

Issa Rae Says She Was 'Horrified' Learning More About Ivanka Trump for New Show 'Coastal Elites'

Issa Rae is opening up about preparing for her new role in Coastal Elites.

In the new HBO quarantine comedy, the 35-year-old Insecure actress plays a philanthropist who runs in the same circles Ivanka Trump.

“For me, this is kind of an education because I do tend to try to avoid as much of the Trump family as possible,” Issa said during the virtual CTAM panel promoting the show via The Wrap. “And Ivanka, in particular, I’ve always found fascinating — but not fascinating enough to listen to.”

“So it took a lot to research,” Issa continued. “And the more I found out, the more horrified I was. And a lot of that is expressed through the work. But a testament to [writer] Paul [Rudnick]’s writing. It was just incredible to read and immediately resonated.”

Issa didn’t elaborate on what she found out about Ivanka.

Directed by Jay Roach, Issa stars in the special alongside Bette Midler, Sarah Paulson, Dan Levy, and Kaitlyn Dever.

According to HBO, “Coastal Elites spotlights five distinct and impassioned points-of-view across the United States. When the shutdown forces these characters to cope in isolation, they react with frustration, hilarity and introspection.”

Coastal Elites will debut on Saturday, Sept. 12 at 8 pm ET on HBO.

Issa Rae To Star & Produce New Movie 'Sinkhole' With Jordan Peele

Issa Rae has teamed up with Jordan Peele for a brand new movie with Universal Studios.

Deadline reports that the film, called Sinkhole, is a “thought-provoking genre movie that engages with questions of female perfection and identity.”

Based on Leyna Krow‘s short story, the movie will focus on a young family that moves into its dream home despite the gaping sinkhole in the backyard.

The mysterious sinkhole manages to fix broken and destroyed things. However, the story asks, what if that thing is a person?

Issa is also in talks to not only produce alongside Jordan, but star in the movie as well.

If you missed it, Issa scored an amazing eight Emmy Award nominations. You can see the full list here…