"This Is the Color I Like My Coffee": Stars Recall Their First Jobs in New York

5:00 AM 4/11/2019

by Bryn Elise Sandberg

Hollywood and media insiders including Tony Hale, Michelle Wolf and Taylor Schilling reveal their first gigs in the Big Apple — private banking assistant, cater-waiter, night-shift doorman — and the occasional indignities involved: "Sometimes I ate food off of people's plates."

Tony Hale, Michelle Wolf and Taylor Schilling
Tony Hale, Michelle Wolf and Taylor Schilling
Dia Dipasupil/FilmMagic; Frazer Harrison/Getty Images; Jerod Harris/Getty Images

  • Michael Kelly

    Actor, 'Tom Clancy's Jack Ryan'

    Getty Images

    "I was a waiter at a restaurant called Sequoia in the South Street Seaport. I remember working doubles Friday, Saturday and brunch Sundays to leave most of the weekdays open for auditions. I was able to make a lot of money, paying off a large chunk of my student loans there. I also remember the restaurant was a big European tourist destination and being one of the handful of waiters who lobbied to have a stamp made in several different languages saying, 'Gratuity not included.' It changed our income con­siderably. The restaurant is now gone but the new Seaport is incredible."

  • Michael K. Williams

    Actor, 'The Wire,' '12 Years a Slave'

    Greg Doherty/Getty Images

    "I used to sweep the floors in the sewing factory that my mother worked at in Bedford-Stuyvesant, Brooklyn. I was 13. All the women used to call me Little Mikey; they would give me all this candy money. I had tons of candy money at the end of the day!"

  • Michelle Wolf

    Comedian

    Tasos Katopodis/Getty Images for Netflix

    "I was an assistant to the CFO of private client services at Bear Stearns on Madison Avenue. My first day, my boss held up a tan-colored journal. He said, 'This is the color I like my coffee. Go get that.' So I did. And I brought it back and he looked at it, and then told the other assistant that had been working there for a while that I matched a color better than her. That made things pretty uncomfortable."

  • Taylor Schilling

    Actor, 'Orange Is the New Black'

    GP Images/Getty Images

    "One of the first jobs I had was taking tickets at the Museum of Television & Radio right around 55th Street before that branch of MoMa opened. I'd work all day Saturday, work all day Sunday and try to have enough money to not eat at the cafeteria every day."

  • Josh Sapan

    President & CEO, AMC Networks

    Noam Galai/WireImage

    "One of my first jobs was working behind the counter at Paley Park, a 'pocket park' with a waterfall in Midtown [3 East 53rd St. between Madison & Fifth], where my big moment was presenting to William Paley himself an assortment of Danish pastries being considered for sale in the park, for him to make the final choice. His pick was from Greenberg Desserts, which is still in business today and is very good."

  • Tony Hale

    Actor, 'Veep'

    Getty Images

    "I was a cater-waiter for most of my years in New York, and I actually cater-waited at Lincoln Center sometimes. The food industry is hard, but I loved cater-waitering. I hated waiting tables because people get so emotional about food, and I would leave there hating the world. But with cater-waitering, they all get the same thing, you didn't have to talk to them, and then at the end of the night, you got to eat all of the food. Sometimes I ate food off of people's plates. Like, I would cut off the piece that they didn't eat and just take the other half! I'm not going to lie, sometimes when I see a [half-eaten] room service tray now …"

  • Ben Smith

    Editor-in-chief, BuzzFeed

    Drew Angerer/Getty Images

    "I delivered chairs for West Side Chair Caning, later shuttered as a fire hazard. It involved a lot of time alternate-side parking the boss' car."

  • Charlie Collier

    Fox Entertainment CEO

    Paul Archuleta/FilmMagic

    "My first job was on 53rd and Third as a sales assistant at TeleRep, earning $1,500 a month. I removed and replaced a lot of staples in ever-growing piles of paperwork. We worked with agency partners on schedules and make-goods for WTTG, a powerful Fox affiliate in D.C. that’s now proudly back in my orbit."

  • Matt Lieber

    Co-founder and president, Gimlet Media

    Matt Lieber (left) with Alex Blumberg
    Matt Lieber (left) with Alex Blumberg
    Jamie McCarthy/Getty Images

    "My first job was as a producer at VH1 Radio at 1633 Broadway and later the 1515 Broadway Viacom HQ. I interviewed classic rock stars like the Moody Blues and Heart."

  • Chris McCumber

    President, USA Network & Syfy

    Courtesy of USA

    "I was a production assistant in 1990 at HA! TV Comedy Network, which became Comedy Central when it merged with HBO's Comedy Channel. I got to work with upcoming comedians like Denis Leary, Jon Stewart and Seth Meyers — who was my boss' assistant."

  • Billy Crudup

    Actor, 'Justice League'

    Getty Images

    "In 1992 or 1993 I waited tables during the summer — while I was in acting school — at a now-closed Italian restaurant on the Upper West Side called Ernie's. My close friend, and fellow North Carolina Tarheel, actor Zandy Hartig, helped get me the job, and while working there I waited on Richard Dreyfuss and Nathan Lane."

  • Willie Geist

    Host, NBC's 'Sunday Today,' and co-host, MSNBC's 'Morning Joe'

    Mike Coppola/FilmMagic

    "I moved to New York from Atlanta in 2004 for a job as a producer on a Fox Sports debate show called I, Max hosted by Max Kellerman, now of ESPN fame. We shot in a tiny studio on 33rd Street that was demolished to make way for Hudson Yards. I worked with lifelong friends like Max, Bill Wolff, Brad Como and Brad Siegel — we had a blast making a show we loved a lot more than our bosses did."

  • Dawn Olmstead

    President, UCP and Wilshire Studios

    Alberto E. Rodriguez/Getty Images

    "One of my first jobs was working on the commercial parodies — aka Film Unit — of Saturday Night Live in 1991. I remember dancing with Sinéad O'Connor at the afterparty the night she ripped up the picture of the pope."

  • Terence Winter

    Screenwriter, 'The Wolf of Wall Street'

    GP Images/WireImage

    "From 1982 to 1984, while attending NYU full-time during the day, I was also the midnight to 8 a.m. doorman at Ruppert Yorkville Towers, an apartment complex at East 91st and Third. We kept a baseball bat under the desk nicknamed 'the Persuader' for any difficult middle-of-the-night visitors."

    A version of this story first appeared in the April 11 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.