50 free Insecure trivia questions with answers — entertainment quiz, new questions added Aug 2026.
Insecure grew out of Awkward Black Girl, the YouTube series Issa Rae funded on Kickstarter in 2011. Co-created with Larry Wilmore and run by Prentice Penny, it premiered on HBO in 2016 and ran for five seasons, following Issa Dee and her best friend Molly through South Los Angeles jobs, break-ups and friendships, with Raphael Saadiq and Solange shaping the sound and Melina Matsoukas the look. This quiz covers the show and the people who made it: the We Got Y'all non-profit, Lawrence's failed start-up, the Stanford backstory, the Rotten Tomatoes scores, the Peabody, the Emmy nominations, the soundtrack albums that led to Rae's Raedio label, and the Netflix deal that made it the first HBO series on the rival service. Fifty questions in sets of ten, from what any fan knows to the details only a completist who has read every cast bio would remember.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Who co-created Insecure with Larry Wilmore and plays the lead?
Issa Rae
The show is partly based on her web series Awkward Black Girl.
Q 02Which YouTube web series was Insecure partially based on?
Awkward Black Girl
Rae raised $56,269 on Kickstarter in 2011 to finish its first season.
Q 03On which network did Insecure air?
HBO
It premiered online via HBO Now and HBO Go on September 23, 2016, before the weekly broadcast began.
Q 04How many seasons of Insecure were made?
Five
The finale aired on December 26, 2021.
Q 05Who plays Issa's best friend Molly Carter?
Yvonne Orji
She landed the role in 2015 without an agent or any real acting experience.
Q 06What is Molly's profession?
Corporate attorney
She has career success but difficulty dating men.
Q 07Issa and Molly have been best friends since their days at which university?
Stanford
Rae herself graduated from Stanford in 2007 in African and African-American Studies.
Q 08What is the name of the non-profit where Issa works in the early seasons?
We Got Y'all
It serves middle-school students of colour.
Q 09Who plays Issa's long-term boyfriend Lawrence Walker?
Jay Ellis
He won an NAACP Image Award for the role.
Q 10Why has Lawrence been slacking in the relationship in season one?
His start-up failed
Issa struggles to reignite the passion in their relationship.
Q 11In which part of L.A. is Insecure set?
South Los Angeles
Rae has been credited with changing perceptions of the area by spotlighting its Black businesses.
Q 12Who is the showrunner of Insecure?
Prentice Penny
He held the job for all five seasons and directed the Netflix film Uncorked.
Q 13Which director of Beyoncé's 'Formation' was an executive producer on the show?
Melina Matsoukas
She introduced Solange to the production as a music consultant.
Q 14Which musician created original music for the first season?
Q 21In which year did the American Film Institute name Insecure a top-10 TV program?
2017
A Peabody followed in 2018.
Q 22Which cast member earned a 2020 Emmy nomination for supporting actress?
Yvonne Orji
Critics often named her the show's MVP.
Q 23Which character does Natasha Rothwell play?
Kelli Prenny
She was also a writer and supervising producer on the show.
Q 24Amanda Seales plays which friend of Issa and Molly?
Raphael Saadiq
He continued to oversee the soundtrack with Rae and supervisor Kier Lehmann.
Q 15Which singer served as music consultant on Insecure?
Solange
Matsoukas, who directed her 'Losing You' video, made the introduction.
Q 16What record label did Rae found after the soundtracks' success?
Raedio
It launched in partnership with Atlantic Records in 2019.
Q 17Which of these artists contributed to the Insecure soundtrack?
Sampha
Goldlink and The Internet were also featured.
Q 18On what date did HBO pick up the pilot?
October 15, 2015
Rae and Wilmore had started work on it on August 6, 2013.
Q 19When did the second season premiere?
July 23, 2017
Season three followed on August 12, 2018 and season four on April 12, 2020.
Q 20The fourth season earned how many Primetime Emmy nominations in 2020?
Eight
They included Outstanding Comedy Series.
Tiffany DuBois
Alpha Kappa Alpha members objected in 2021 to her character wearing the sorority's insignia.
Q 25Who plays Daniel King, Issa's on-and-off love interest?
Y'lan Noel
He was a main cast member in seasons two and three.
Q 26Kendrick Sampson plays which character from season three onward?
Nathan Campbell
Sampson was previously known for The Vampire Diaries and How to Get Away with Murder.
Q 27Alexander Hodge plays Andrew Tan, a love interest of which character?
Molly
He was promoted to the main cast for season four.
Q 28Who plays Frieda, Issa's co-worker at the non-profit?
Lisa Joyce
She was a main cast member for the first three seasons.
Q 29What Rotten Tomatoes rating did the first season receive?
100%
The fifth season also scored 100%.
Q 30Which channel began airing the series in syndication in February 2023?
OWN
It aired two back-to-back episodes at a time.