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Abbi Jacobson Imagines What's Inside the Bags of Oprah, Kanye and Donald Trump

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Astrid Stawiarz/Getty

Broad City‘s Abbi Jacobson has always been fascinated by the things people choose to carry with them  even the mundane junk, like burrito punch cards, loose bobby pins, deodorant and hot sauce.

“Especially someone who lives in New York, you sort of have to pack for the day a little bit more. People who drive can leave so much more in their car. You realize, ‘Oh, my day is a little bit better when I have this with me and I don’t have to like, buy it,’” Jacobson tells PEOPLE. “It’s always been fascinating to me how people pack their stuff and what they carry around with them.”

She suspects that the inspiration for Carry This Book (out Oct. 25), her illustrated look inside the bags of famous people, came to her when reading Tim O’Brien’s The Things They Carried in middle school. The novel tells the stories of Vietnam vets through the items they carried around with them during the war.

“I thought, ‘Wow, what a cool way of giving details and clues into what who these people are.’ And voyeurism is something that we’re all so interested in,” she says. “Even with your friends you’re like, well, let me see what’s in here. Medicine cabinets, too. Everyone’s interested in these secret worlds we have.”

But rather than find out the real contents of everyone’s carry-ons, Jacobson took a whimsical guess at what might be inside. Carry This Book illustrates the bags, sacks, purses and backpacks of famous pop cultural and historical figures, from the lowest brow to the highest brow, including Benjamin Franklin, Prince, Beyoncé and even her Broad City character, Abbi Abrams. This isn’t to say that the book is pure fiction Jacobson drew from real facts she knew about her subjects. Kanye West, for example, is on record as loving Fiona Apple, which is why the flash drive she illustrated for him has a specific “Fiona Apple” folder.

Kanye’s bag:

Abbi Jacobson

“Kanye’s was conceptually one of my favorites because I would love to know what folders are on his desktop. I find the most normal things about famous people to be the most fascinating. Because we all label our folders on our flash drives and our desktops and have these things that we collect virtually, too. The way we organize our things is so interesting to me,” she says.

Obviously, Jacobson finished the book a few months ago, which means that she might have tweaked some of the more topical figure’s illustrations — like Donald Trump, for example, about whom new information has obviously come out.

“The Trump page I would add to,” she says of some of the photos she might edit now. “I don’t like what Ruth Bader Ginsburg said recently, but I’m like, ‘What would I have changed [with hers]?’ It’s hard with people. People are always saying stuff.” (It’s true. People say stuff constantly.)

Trump’s bag:

Abbi Jacobson
Abbi Jacobson

The book, colorful and legitimately hilarious, also includes some practical organizing tips, like this one: Whenever you travel, bring a plastic bag with you for your dirty clothes.

“That’s directly from my mom. I call her Monica because she’s like Monica on Friends with packing and stuff. You really can’t go wrong with the plastic bag,” she says.

Oprah’s Bag:

Abbi Jacobson
Abbi Jacobson

As for the contents of Jacobson’s own bag, the schlep varies each day. When we spoke with her on Tuesday, she revealed the insides of her backpack, which was gloriously lightweight because she didn’t have to lug her computer around. (“A day when I don’t have to carry my laptop around is a good day.”)

“I don’t have the most interesting stuff on me right now. I have all these little travel-size hairsprays with me because I’m about to go on the road for this book tour, and I’ve become really into this Oribe hairspray,” Jacobson says. “It gives a little wave. Then I have thank you cards I have to write today for everybody doing Q&As with me. I’m carrying my friend Phoebe [Robinson]’s new book, You Can’t Touch My Hair. It’s so funny. I’ve got a notebook. I’ve got a free pens. I always have a good pen with me. Lipstick. You know, the basics.”