Saturday, November 26, 2022 Nov 26, 2022
53° F Dallas, TX

Q&A With National Magazine Award Winner Skip Hollandsworth

By Tim Rogers |

Last week I did a Q&A with Texas Monthly‘s Skip Hollandsworth right before he went up to NYC for the National Magazine Awards. Turns out, the guy actually won. So let’s do it again. Jump to find out how hard Skip partied after he won magazine writing’s biggest award:

1:59 PM me: You there?
texmoskippy: Yes.
me: So you’re going to keep this Gmail address I set up for you? That’s great, because you’ll never figure out how to change the password, so I’ll always be able to check your mail.
2:00 PM texmoskippy: Of course I’m going to keep it. I’m also in the process of hiring a libel lawyer who will be watching to see what you write on it.
2:01 PM me: Oh, wow. I hadn’t even THOUGHT about the fun I could have sending email as you. Genius.
2:02 PM texmoskippy: The drawbacks of being a celebrity. Okay, a minor celebrity. Okay, I was a tiny media celebrity for about fifteen minutes last week, and it’s already gone — long, long gone.
me: Okay, so take me to the Big Apple and the night of the National Magazine Awards. Did you rent a tux, the whole nine?
2:04 PM texmoskippy: Just black suit. The NY media crowd disdains tuxedos. Lots of guys were there in the obligatory new fashion (what the name of that fashion is, I have no idea) in which they wear expensive dark suit, nice shirt, but no tie. Chris Anderson, editor of Wired, had that very look, except that his shirt was not ironed, giving him that hip tech image, I suppose.
me: Who was at your table?
2:05 PM texmoskippy: No tables. We’re at one of the Lincoln Center auditoriums, sitting in a row, staring up at stage, just like Academy Awards — except that none of us are good looking.
2:06 PM me: That doesn’t sound like much fun. Was there a cocktail hour or something beforehand where you could tell people who you were and point out Dallas to them on a map?
2:10 PM texmoskippy: I strolled in, arms wide, ready to say, “Yes, it is me, Skip Hollandsworth from Dallas,” but not one person looked my way. Very insular group, those NY media-ites. I spoke to the two people I knew — Mark Seal, former Dallas Morning News reporter turned famous Vanity Fair writer who was up for award, and Bryan Burroughs, Temple Texas native turned famous Vanity Fair writer who was up for award -and they did their very best to pretend they remembered me. But my 13 year old daughter Tyler one upped me. She walked right up to Anna Wintour, who was getting some lifetime achievement award and she said – and I swear this is truue — “Miss Wintour. I’m Tyler Hollandsworth and I just want to say I love your work.” I don’t know where the hell that came from. She’s never opened a Vogue in her life. (She has watched the Devil Wears Prada movie, however, so maybe that’s the connection.) Wintour, who was not wearing sunglasses for once — and my God her eyes are beautiful — gave Tyler a look, then her gaze drifted away as she said “Thank You.” Tyler walked back to the TexasMonthly crowd, shrugged her shoulders and said, “I was dissed.”
2:12 PM me: That slays me. Your daughter is my hero.
2:13 PM texmoskippy: I then suggested she walk up to Graydon Carter and say, “Hey, Tim Rogers wants to send you his resume,” but she refused. She has ethics, she says.
me: I now hate your daughter.
So when they get around to your category, tell me what was going through your mind. As big as your ego is, I really did believe you when you told me you didn’t expect to win. But some part of you had to be hoping, right?

6 minutes
2:20 PM texmoskippy: I was the first category in the show. I had barely taken my seat, apologized to the man in front of me for nervously kicking the back of his chair and making gurgling sounds in the back of my throat, and out comes Martha Stewart to make the presentation for feature wriring. My first thought was, “The woman must be 7 feet tall.” She’s got killer legs. I leaned over to the guy beside me and said, “Hey get a look at those gams,” and she suddenly is announcing the nominees. Then she rips open the envelope and announces my name. I wasn’t even slightly prepared. I just sat there, like an idiot. Then Jake Silverstein, Texas Monthly’s editor — who by the way is speaking tomorrow night at Legacy Books, reading from his riveting new book “Northing Happened and Then It Did,” which I’m reading right now like a crazed man so I can tell him when I see him tomorrow night that the book is fantastic — stood up and gave a nice speech about me, Skip Hollandsworth, of Dallas, Texas.
2:22 PM Oops, misspelled Jake’s book. It’s “Nothing Happened and Then It Did.” By the way, what happens when you read your editor’s book and realize he’s a far, far better writer than you are. Now, you have to do what he tells you about changing your stories. This is going to be a difficult few years. But I will have the book finished by tomorrow night. One trick to all you pepole out there: when you compliment someone on their book, make a reference to something he or she wrote in the last chapter so you won’t be exposed as one of those frauds who just read the introductio.
Oops, I mean to say “introduction.” I still hate this instant messaging. There should be spell check for this stuff.
2:23 PM Oops, I meant to have a questio mark after the sentence, “By the way, what happens when you read your editor’s book and realize he’s a far, far better writer than you are…..”
2:24 PM me: Stop correcting yourself. People understand you’re IMing.
texmoskippy: Oh, my God and I left the ‘n” off “question.”
me: But so I don’t get why Jake gets up to make a speech about you. That’s not the way the Academy Awards work. Shouldn’t YOU get up and say a few words. You know, thank the little people?
2:25 PM texmoskippy: I loved it actually. I could just sit back with the glass of wine I sneaked into the hall and watch the show. Obviously, if I gave a speech, I would do nothing but constantly correct my grammatical mistakes I had just made
2:26 PM me: (PS: I refuse to read Jake’s book until it’s available on iBooks. That’s my excuse.)
texmoskippy: What’s iBooks?
2:27 PM me: Did you sit through the rest of the awards or — as I’d bet money you did — get the hell out of there and start throwing back whiskey like a man possessed?
texmoskippy: No, sat through everything, including Best Fact Cheker and Best Receptionist of the year.Best Fact Check
2:28 PM me: After the gig was over, though, you got the hookers and the blow and the rest, right?
2:30 PM texmoskippy: This is what I like to call the TRM — the Tim Rogers Moment. You have this very pleasant conversation with you — enlightening, actually –and suddenly, inevitably, out comes your hooker and blow reference. Sad. So, so sad.
2:33 PM me: And yet, like any badass catchphrase — “Whatchew talkin’ about Wills?” comes to mind — no episode is complete without it.
2:34 PM And I take your evasive answer to mean that you’re still calling bars in Manhattan, trying to find your credit card. And you and Jake now have matching tattoos. Etc., etc. Am I right?
2:36 PM texmoskippy: No, weirdly that was Jake on the phone just now, asking if I could take him from somewhere to Legacy books. I’m thinking, “Beautiful, you win a National Magazine Award, you still have to be a chauffeur for your boss.”
me: Please tell me you’d arranged for a sitter and Tyler didn’t see Debauched Daddy.
2:37 PM texmoskippy: After the presentation, the Texas Monthly people went to dinner and then everyone straight to the hotel. You would have been bored out of your mind.
me: Talk about sad.
Okay, here’s my takeaway:
2:38 PM 1. TexMo people don’t know how to party. 2. Your daughter is a better reporter than you are. 3. Anyone at all can win a National Magazine Award. And 4. Jake is reading tonight at Legacy Books.
That about sum it up?
2:39 PM texmoskippy: Wait. One more thing that’s sad. Today, I’m trying to figure out how to write a simple 2,000 word column for July issue. (June issue, as you remember from last talk, is about my trip to the state hospital. I’m sure you’ll buy the issue just to read me.) Anyway, I have no idea what to do. I’m panicking. Life, again, is back to normal.
me: Just do what you do best, Skip: write about yourself.