Interview: Matt Singer Returns to Discuss His New Book ‘Funny Business: The Old-School Wedding Crashers and Knocked-Up Virgins Who Changed Comedy Forever’

Multi-hyphenate Matt Singer has been a colleague of mine since I began my writing career, nearly 20 years ago. His articles, podcast, and reviews are always a pleasure to read, and this is coming from someone who doesn’t read a whole ton of his fellow colleagues’ work. Suffice it to say, when Singer writes something, I’m in. The fact that his newest book, Funny Business: The Old-School Wedding Crashers and Knocked-Up Virgins Who Changed Comedy Forever, coming on the heels of his wonder prior book  Opposable Thumbs: How Siskel & Ebert Changed Movies Forever, is about another subject beloved to me, well that’s just an added bonus. I’d read almost any book about the raunchy comedies I love, just like I would have read anything about  Roger Ebert and Gene Siskel. That it’s from Singer only makes it more of a must-read. Recently, I got on Zoom with him to talk about the new book, as well as the research that went into it. Today, that discussion comes your way.

This is the official description for Funny Business: The Old-School Wedding Crashers and Knocked-Up Virgins Who Changed Comedy Forever, via the publisher:

A celebration of a generation of iconic comedies—the raunchy, blockbuster “Frat Pack” films of the early 2000s—and a no-holds-barred look at their rise and fall in Hollywood, the effects of which can still be felt in the fractured media landscape of today

If you were a moviegoer in the early aughts, you had a front-row seat to a golden age of comedy. Ben Stiller, Seth Rogen, Will Ferrell, Owen Wilson, Steve Carell, and Vince Vaughn became unlikely leading men—a band of rowdy wedding crashers, hungover bachelors, and 40-year-old virgins dubbed the “Frat Pack” that took Hollywood by storm over the span of a single decade. Then, seemingly overnight, Frat Pack movies vanished. Or did they?

In Funny Business, award-winning author and film critic Matt Singer traces the path these gonzo stars and directors took from the fringes of comedy to the mainstream—beginning on tiny stages like Second City and the Groundlings, then infiltrating into talent incubators like SNL, eventually leading to the big screen. Along the way, he shares insider stories of the films that raised a generation, including: The 40-Year-Old Virgin, Zoolander, Borat, Anchorman, Old School, and The Hangover.

How did these movies and their stars come to dominate a generation of moviemaking? Who won—and who was left out—of this comedy boom? And can studio comedies make a comeback in our modern digital and streaming world? Funny Business points the way forward to a (possible) new future for cinema—never forgetting that the audience always gets the last laugh.

Below, you can hear my chat with Singer. We talk about what he included in the book, what he didn’t, and how it all came together. Much like with his prior book, the process of it all, given the huge amount of material at his disposal, fascinated me. He’s open and honest about everything, and it leads us down some interesting paths, so hopefully it gets you even more interested in reading his latest work. You can buy the book here or wherever you get your favorite reading materials. It’s out tomorrow and well worth your time…

Here now is my interview with Funny Business author Matt Singer. Enjoy:

Funny Business: The Old-School Wedding Crashers and Knocked-Up Virgins Who Changed Comedy Forever is available to buy tomorrow!