Bossypants

I came to Bossypants late, after years of seeing Tina Fey quoted in speeches and memes without reading her in full. Published in 2011 by Little, Brown and Company, about 277 pages, it is her memoir in essays, from childhood in Pennsylvania through Second City and Saturday Night Live to 30 Rock and early motherhood. I read it on a plane and laughed out loud twice, which embarrassed me in a good way. What I liked most was not the famous impressions but the work stories, how writers rooms run, how sketches live or die, how a woman holds authority in rooms built for men. It is light but not empty, and it annoyed me in a few spots too.

Growing up Fey in Pennsylvania

Fey opens with family, and these are my favorite pages. She grows up in Upper Darby, Pennsylvania, daughter of Don Fey, a earnest man who worked in publishing and loved history, and Zenobia Xenakes, a sharp Greek American woman who worked in a brokerage and kept the house on schedule. Her older brother Peter teases and protects her. Their house is orderly and funny, full of rules and jokes. She describes herself as a serious kid with glasses and a strong sense of right and wrong, the kind who reads the manual and reports cheaters.

School stories pile up fast. She is good at classes, bad at sports, watchful at dances. She writes about a scar on her face from a childhood attack by a stranger in an alley, and she handles it with a brief directness that stops the jokes for a page. She does not mine it for pity. She states what happened, notes how adults tried to make her feel normal, and moves on. That choice tells you a lot about her style. She will share a hard fact, then steer back to work and jokes rather than linger.

Comedy enters through television and church plays and school shows. She loves compliance and punch lines at the same time. She watches Saturday Night Live as a teen and memorizes who writes what. She goes to the University of Virginia, studies drama, learns to type fast, graduates without a clear path, and drifts toward Chicago because that is where improv lives. Her parents worry in a loving way. Her father drives her to auditions and helps with rent talk. Her mother tells her to keep her standards high and her hair neat. Fey writes about them with clear love, even when she mocks their thrift and worry. I smiled at the portrait of Don keeping newspaper clippings and Zenobia offering blunt advice about men and money.

Chicago, improv, and learning to fail loud

Chicago is where Fey learns her craft, and she writes these chapters like a grateful student. She joins the Second City world, first taking classes, then touring, then landing on the main stage. She describes improv rules with the zeal of someone who still believes in them, say yes and build, listen hard, make your partner look good, commit even if the scene is about dishwashers in space. She names teachers and teammates, including Rachel Dratch, with whom she shares a small apartment and long bus rides. Money is thin. Apartments are cold. Shows are late. She loves it.

She is honest about being bad at first. She talks too fast. She tries to be clever instead of clear. She learns to play mothers and secretaries and anchors because she looks reliable, then learns to break that type by adding bite. She describes a show where a joke dies so hard the room feels airless, and how the cast saves it by heightening the failure into a new game. Those nights teach her more than easy laughs. She starts to trust ensemble over solo sparkle, to write to the strengths of the group, to take notes without sulking. I found this the most useful part for anyone who works in teams, even outside comedy.

Touring with Second City brings road stories, small towns, college gyms, drunks in front rows. Fey and Dratch do a two woman show and learn to read a crowd in seconds. Fey writes about sexism on the road, club owners who assume the women are assistants, male improvisers who talk over tags. She answers with work rather than speeches, by getting funnier and more precise. She meets Jeff Richmond, a pianist and composer who will become her husband, and she writes about him with a plain fondness that avoids gush. He gets her hours. He makes her laugh backstage. Their courtship is mostly jokes and late food, which feels right for two theater people.

Saturday Night Live and the writers room

Fey moves to New York in 1997 as a writer for Saturday Night Live, hired after a submission packet that showed she could write sketches and jokes in many voices. She describes the building at 30 Rockefeller Plaza as thrilling and grimy, full of narrow offices and coffee cups. Lorne Michaels hires her and watches from a slight distance. She shares an office, stays up past midnight on Tuesdays rewriting, and learns that a sketch can be loved on Monday, rewritten on Wednesday, cut on Saturday afternoon, then revived for dress rehearsal. The pace is brutal. She thrives on it for a while because she likes deadlines.

She becomes head writer in 1999, the first woman to hold the job, and she writes about the title with pride mixed with wariness. She does not want to be a symbol all day. She wants to fix sketches. She describes pitch meetings where men shout over each other, and how she learns to speak short and firm to be heard. She hires more women and pushes for sketches that let women be weird rather than wives. She writes about working with Jimmy Fallon on Weekend Update, their different energies, his charm and her bite, and how they built a rhythm of jokes and banter. Later she anchors with Amy Poehler, and those shows crackle because the two trust each other completely.

Backstage portraits fill these pages. Molly Shannon, Will Ferrell, Chris Parnell, Horatio Sanz, Maya Rudolph, all get warm sketches. Fey tells how Ferrell would commit to a silly cowbell part until the room broke, how Shannon would stay in character through a wobble, how Rudolph could sing anything. She explains the jobs no viewer sees, cue cards, dressers, makeup artists who fix wigs in seconds. She tells of a sketch about a talk show that dies in dress and is saved by a single line change. For a fan of the show, these details are gold. For a writer, they read as field notes on revision under pressure.

30 Rock, motherhood, and the Sarah Palin weeks

Leaving Update to make 30 Rock is the book's second act. Fey creates a sitcom about a sketch show, playing Liz Lemon, a harried writer who loves sandwiches and hates small talk. She writes about building the show with Robert Carlock, casting Alec Baldwin as Jack Donaghy, Tracy Morgan as Tracy Jordan, Jane Krakowski as Jenna, Jack McBrayer as Kenneth. She describes the pilot process, network notes, bad test scores, and the slow find of tone in season one. Baldwin brings old school polish. Morgan brings wild invention that scripts can barely hold. Fey learns to write shorter scenes to fit his timing and to let Baldwin's long speeches run because he earns them.

Motherhood runs alongside work, and Fey writes about it without gloss. Her daughter Alice is born in 2005, and Fey returns to work fast because that is what her job demands. She describes pumping in a small room between rewrites, bringing the baby to set, feeling guilty and proud in quick turns. She mocks the advice she gets about balance, saying balance is a lie told by people with staff. She praises her husband Jeff for doing night feeds and school runs without making it a favor. She also admits help, paid sitters, family visits, a job with money. That honesty saves these chapters from lecture. She is not saying every mother should do as she did. She is saying this is what her choice cost and gave.

The Sarah Palin stretch in 2008 gives the book its most famous story. Fey is asked to play the Alaska governor on SNL during the election because of a physical likeness and a gift for tone. She describes the rush, wigs fitted in hours, lines rewritten as Palin gives interviews, the live shows with Amy Poehler as Hillary Clinton. The sketches draw huge ratings and sharp criticism. Fey says she tried to play the words as written by Palin herself, letting quotes carry the comedy. She writes about hate mail and praise mail arriving together, about being blamed for the election by both sides, about going back to 30 Rock on Monday tired to the bone. I liked that she resists claiming victory. She treats it as a strange assignment that landed at the right time.

Tours, photo shoots, and the strange job of fame

Fame arrives sideways in this book, and Fey writes about it like an anthropologist stuck inside the ritual. After 30 Rock finds its audience, she is asked to host award shows, pose for magazines, and give advice speeches at colleges. She describes sitting in hair and makeup for two hours to look natural, then standing on a red carpet while strangers shout her name and tell her to tilt her chin. She hates the shoes. She likes the free food. She learns to answer the same five questions with fresh jokes, about Liz Lemon, about working with Baldwin, about whether comedy is hard for women.

One long riff covers a trip to do press, with early call times, cold vans, and radio hosts who have not seen the show. Fey and her cast mates learn to sell episodes in thirty second bursts. Morgan goes off script and charms everyone. Krakowski sings a line to fill dead air. McBrayer stays sunny through take after take. Fey watches and takes notes, because she is still a writer first. She later uses those road hours as material, turning junket fatigue into Liz Lemon stories about press days that go wrong.

She also writes about money with unusual candor for a star memoir. She tells young comics to open a savings account early, to keep a day job as long as possible, to learn how health insurance works before quitting. She remembers earning little at Second City and stretching pizza for days. She remembers her first SNL raise and how fast taxes and city rent ate it. When 30 Rock money comes, she banks it and keeps the same winter coat. Her father Don would approve. I liked these passages because few memoirs admit that art careers run on cash flow and that talent helps less if rent is late.

The advice speeches collected here show her voice at its best and most strained. At one college she tells women to keep their own schedule, to say no to unpaid work that leads nowhere, to find friends who tell the truth about a draft. At another event she jokes about Spanx and false lashes until the joke wears thin, then lands a plain line about doing the work when no one watches. You can feel the rooms laughing. You can also feel Fey tired of being asked to solve sexism in eight minutes with jokes. She does what she can, which is to be specific about her own path rather than pretend it fits all.

What holds up and what feels thin

The last essays jump around, which suits Fey. She writes about beauty rules for women on camera, the daily pressure to be thin and smooth and young while men are allowed to age into bosses. She tells of makeup chairs where she is told to fix her face, of photo shoots where she is posed like someone else, of awards shows where her dress matters more than her script. Her answer is comic refusal, to show up as herself, to joke about the rules while playing by enough of them to stay employed. Some readers will find this too mild. I found it honest about trade offs, though I wanted more anger at the system that sets those rules.

She writes about fathers and daughters, about raising Alice to be strong and funny, about telling young women to do their work and keep their own money. She includes a long section of hate mail and a fake prayer for a coworker, both very funny, and a chapter on her honeymoon and travel that is slighter. The honeymoon pages drift, pleasant but loose, and a few one liners repeat. The book's shape shows its origin as essays and speeches stitched together. Some seams show. A tighter final third would have helped, with fewer lists of thanks and more scenes like the early Chicago nights.

My fair criticism is this. Fey can hide behind jokes when a harder look would serve. She touches on race in writers rooms but moves past fast. She touches on class in comedy careers, who can afford unpaid years in Chicago, then moves on. She is generous to bosses like Lorne Michaels, which is loyal but leaves questions about power unasked. And some humor has aged, a few jokes about looks and sex that read meaner now than in 2011. Still, the core holds, a smart worker telling how she learned to lead a room, to write under fire, to be the boss without copying the men before her. I closed it liking her more, not as a star but as a colleague I would trust on a deadline.