Angry Optimist: The Life and Times of Jon Stewart
Lisa Rogak
Biography
225 pages
Published 2014

So I’m a little ambivalent about this book. Jon Stewart took over at The Daily Show the same year I graduated high school. I was 16 and only starting to pay attention to politics. I was also raised quite conservative Christian – the pundit we listened to the most was Rush Limbaugh. And here was a man saying things that were the total opposite of what I’d been taught – but also things that resonated a lot more with me. Many years later, when The Daily Show and Jon Stewart were labeled the most trusted voices in news media, I had no trouble at all believing it. He not only knew how to speak to my generation, he also spoke for us. All the things we were thinking, he was out there shouting. He was our window into this grown up, corrupted world of politics, and we loved him for it.

Not to say he’s perfect. I’d heard – and Angry Optimist mentions – that he can occasionally be a rage-filled asshole. That the staff of The Daily Show has a woman problem. (As in, not enough of them, and can’t keep them.) So while I do admire the man, I am not blind to his flaws.

The book is interesting – I learned more about his early life and career – but nothing really game-changing. And perhaps that says something about Stewart. There aren’t really any skeletons in his closet, or scandalous stories. He’s just an angry Jewish comedian.

Rogak’s style of writing is easily consumed; I read the entire book in about three hours. Perhaps part of why I find it so anticlimactic is that she ends it with this sense of not knowing what Stewart might be up to next, and whether, if he does decide to leave The Daily Show eventually, if the show will end with him – and we know those answers now, three years after the book was published. Stewart has retired (barring the occasional appearance on Colbert’s show) and Trevor Noah is doing an admirable job of holding down the fort after Stewart’s exit. (With less anger, and a little more befuddlement, which is a fun change.) I was also a little disappointed that she mentions Stewart’s friendship with Anthony Weiner – but doesn’t say anything about how he took the ribbing from Stewart over Weiner’s rather unglamorous exit from politics.

I have also heard that the audio book is not good – apparently the narrator is boring. So I’d recommend the print book over the audio, if you choose to read it.

From the cover of Angry Optimist: 

Since his arrival at The Daily Show in 1999, Jon Stewart has become one of the major players in comedy as well as one of the most significant liberal voices in the media. In Angry Optimist, biographer Lisa Rogak charts his unlikely rise to stardom. She follows him from his early days growing up in New Jersey, through his years as a struggling stand-up comic in New York, and on the short-lived but acclaimed The Jon Stewart Show. And she charts his humbling string of near-misses – passed over as a replacement for shows hosted by Conan O’Brien, Tom Snyder, and even the fictional Larry Sanders – before landing on a half-hour comedy show that at the time was still finding its footing amidst roiling internal drama. 

Once there, Stewart transformed The Daily Show into one of the most influential new programs on television today. Drawing on interviews with his current and former colleagues, Rogak reveals how things work – and sometimes don’t work – behind the scenes at The Daily Show, led by Jon Stewart, a comedian who has come to wield incredible power in American politics.