While Chicago’s The Second City is famous for launching comedy legends onto Saturday night television and Hollywood movie screens, the theater’s alumni have also produced some of the sharpest, most bestselling literature in modern publishing. Trained in narrative structure, character observation, and razor-sharp dialogue, Second City veterans make naturally brilliant authors.

Below, we rank the 8 best books written or co-written by Second City alumni, featuring masterworks by Paul Dinello, Stephen Colbert, Amy Sedaris, and Tina Fey.

1. ‘Wigfield: The Can-Do Town That Just May Not’ (2003)

  • Authors: Amy Sedaris, Paul Dinello, and Stephen Colbert
  • Why It Ranks #1: A tour-de-force of satirical fiction. Chronicling the impending destruction of a bankrupt small town through the eyes of a vain journalist (played by Dinello), Wigfield is a pitch-perfect skewering of American journalism and rural decay, lavishly photographed by Todd Oldham.

2. ‘I Am America (And So Can You!)’ (2007)

  • Author: Stephen Colbert (with Paul Dinello and The Colbert Report writing staff)
  • Why It’s Essential: Spending months atop the New York Times Best Seller list, this book perfectly translated Colbert’s conservative cable news blowhard persona into print, featuring hilarious margin notes, ideological flowcharts, and satirical essays on religion, family, and politics.

3. ‘Bossypants’ (2011)

  • Author: Tina Fey
  • Why It Matters: Tina Fey’s memoir details her rise from Second City Chicago to becoming Saturday Night Live’s first female head writer and creator of 30 Rock. Insightful, feminist, and relentlessly funny.

4. ‘Simple Times: Crafts for Poor People’ (2010)

  • Authors: Amy Sedaris (with Paul Dinello)
  • Why It’s a Cult Classic: A hilarious parody of lifestyle crafting manuals, offering step-by-step instructions on making wind chimes from rusty nails and centerpieces from expired sausage meat.

Complete Top 8 Rankings

Rank Book Title Year Authors / Alumni Genre
1 Wigfield 2003 Amy Sedaris, Paul Dinello, Stephen Colbert Satirical Fiction
2 I Am America (And So Can You!) 2007 Stephen Colbert, Paul Dinello & Staff Political Satire
3 Bossypants 2011 Tina Fey Memoir / Humor
4 Simple Times: Crafts for Poor People 2010 Amy Sedaris & Paul Dinello Parody Craft Book
5 I Like You: Hospitality Under the Influence 2006 Amy Sedaris Entertaining Guide
6 America Again: Re-becoming The Greatness 2012 Stephen Colbert & Staff Political Satire
7 Yes Please 2014 Amy Poehler Memoir / Essays
8 Something Wonderful Right Away 1977 Jeffrey Sweet (Oral History) Second City History

The Second City Literary Trademark

What links every book on this list is a profound respect for voice. Because these authors spent years training on stage listening to audience reactions, their written prose reads with the cadence, rhythm, and timing of live speech.

Further Reading