Bossypants – Tina Fey

Bossypants – Tina Fey 

Tina Fey’s Bossypants is more than a celebrity memoir — it’s a masterclass in how to turn awkward childhood memories, tough career lessons, and feminist observations into laugh-out-loud comedy. Written in Fey’s signature smart, self-aware voice, the book is a combination of personal essays, behind-the-scenes anecdotes, and practical-but-hilarious life advice.

The book opens with Fey’s early life, including growing up in suburban Pennsylvania as a nerdy, theatre-obsessed kid. She writes about getting a scar on her face as a child — not in a melodramatic way, but with humor and self-deprecation that immediately sets the tone for the rest of the memoir. Fey’s ability to make even painful experiences funny is one of the book’s greatest strengths.

From there, Bossypants dives into her years at Second City, where she learned the rules of improv — rules she later applied to life. One of the highlights is when she explains the concept of “yes, and,” which encourages performers to accept whatever is offered in a scene and build upon it. She cleverly connects this to career and personal growth, suggesting that life works better when you say yes to opportunities and add something of your own.

A large portion of the memoir is dedicated to her time on Saturday Night Live, where Fey became the show’s first female head writer. She shares juicy but good-natured behind-the-scenes stories, like what it was like working with Lorne Michaels, how sketches come together in a single week, and the pressure of doing political impressions (including her now-legendary Sarah Palin). She does all of this without ever sounding mean-spirited — a rarity in celebrity memoirs.

Another standout section covers her experience creating and starring in 30 Rock, including how difficult it was to get a female-led, absurdist sitcom on network television. She talks about casting Alec Baldwin, writing Liz Lemon as a version of herself, and balancing work and motherhood — sometimes failing hilariously.

One of the most memorable essays is her open letter responding to internet trolls and critics of her appearance. Instead of anger, she uses humor as a shield, writing that she doesn’t have time to care about strangers’ opinions because she’s too busy living her life and raising a child. This section became a rallying cry for women facing online harassment and remains one of the most quoted passages from the book.

Fey’s humor style is witty, self-deprecating, and full of sharp observations about gender politics, the entertainment industry, and human behavior. Her jokes are layered — sometimes subtle, sometimes absurd, but always smart.

Why Read It: Bossypants is perfect if you want to laugh but also learn something about resilience, creativity, and saying “yes” to life. Tina Fey’s honesty about her insecurities makes her stories relatable, and her comedic timing on the page is just as good as it is on screen.