- Ascended Meme: On September 18, 2020, Keke Palmer had jokingly tweeted about making an appearance in season 5 after expressing excitement about its release. Come the release of the first trailer for season 5 in 2021, and it's revealed that Keke does show up in an episode as Condola's sister.
- The Danza: Issa Rae plays the character Issa Dee.
- Fake American: Alexander Hodge (Andrew aka Asian Bae) is Australian, playing a native of Los Angeles.
- Real Life Writes the Plot: Condola's actress, Christina Elmore, was actually pregnant around the time Condola announced HER pregnancy to Lawrence.
- Saved from Development Hell: As early as 2011, Awkward Black Girl creator Issa Rae met with network executives to bring the web series to television. However, Rae faced Executive Meddling from the network execs, who wanted to Race Lift the main character to white. Eventually in 2013 it was announced that Issa Rae would be teaming up with Larry Wilmore to create a pilot for HBO, and Insecure premiered in 2016.
- What Could Have Been: Issa Rae wrote in her memoir that, as previously stated, network executives wanted to recast the lead from Rae herself to either a white character or the much lighter-skinned Lauren London.
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