Blog Newsletter Syndicate

Riding the Rails

Here’s another flashback from my cartoonist buddy, Randy Enos. Like Randy, I also lived in Connecticut’s and took the train into Manhattan to visit art directors and deliver my art –back in the 1980’s (for me), and earlier, that was the thing cartoonists did. After Federal Express and fax machines came into being, illustrators and cartoonists moved away and the Manhattan cartooning and illustration culture was lost. I miss it.  –Daryl

The name of our train station in Westport is “Westport Saugatuck” or, as one wag of a conductor once announced … “WESTTUCK and SAUGAPORT”.

What’s in the bag?

I loved riding the old trains before they started looking like subway cars with the sliding doors. We used to have to climb the steps up into the train and when I would hop on about noontime, I was able to go into the dining car and eat a hearty hot lunch (or dinner as we called it when I was very young). My favorite thing was to relax in the dining car watching the landscape whirring by while a waiter would bring me my meatloaf and mashed potatoes and gravy and apple pie for dessert. For years, I was a night worker going to bed at 4 in the morning and waking up about 10 or 11 and hopping on that train to deliver work and pick up more in New York City. At the New York Times, for instance, the art directors didn’t even get in to work until noon.

It was either you got on the train to deliver a job or you could give a train conductor five bucks to deliver it for you in the city on his break as soon as he got to Grand Central. It wasn’t unusual to see, on the platform, a stubble-faced sleepy-looking illustrator wearing a bathrobe and clutching an envelope with his art in it looking for a willing conductor. The other thing we would do was to use the services of Ryder’s Stagecoach to deliver our art. You could take your work to Ryder’s house at any time in the early morning, like 3 or 4 and you’d go to the back screen door and quietly stick it in there for him hopefully without waking the dog. That damn dog would often wake up and bark, though.

Randy’s wife, Leann, with Randy’s 6 foot Black Indigo.

When I worked at the Famous Artists School, we would get a 3 week vacation in the summer. In my 8 years working there, I never took a vacation. I would, instead, take my vacations one day a week and use that day to go to the city to see art directors and try to sell my work.

I had pet snakes, a 6 foot Black Indigo and a 5 foot Gopher Snake. I used to take them to New York with me sometimes because my art directors wanted to see them. We’d let them slither down the hallways past the shocked secretaries at NBC.

One day, I was sitting on the train with the white laundry bag containing my 6 foot snake resting quietly on my lap as the conductor approached punching tickets. He knew me very well and often would just make believe he was punching my ticket, thus giving me a free ride. That day, as he was reaching across me to punch the ticket of the lady to my right, the snake, “Satan,” rippled in the bag. The astonished trainman said, “Randy –I do not want to know what you have in that bag!”

One time, because the trainmen knew my wife and I so well (they would often sit and talk with us when they weren’t picking up tickets) that they let Leann drive the train home. My wife was an actress and she travelled the train a lot too.

On Thursdays, I would sit with all the New Yorker cartoonists going in to show their roughs. My neighbor, Don Reilly, was always there with his friend Dana Fradon and sitting across the aisle from us would be Whitney Darrow or Bob Weber (who never had his roughs done and would do them on the train). One time I watched Whitney off to the side on the train platform in Westport, drawing a guy waiting for the train. Later, that same day, I encountered him hiding in a doorway, way uptown in the city, surreptitiously drawing a lady waiting for a bus.

Along with the artists, the morning trains out of Westport carried most of the Madison Avenue advertising world. On the way home, we often had to ride in what we called “cattle cars” which had no windows and no seats. I used to see some of the richest tycoons of advertising, finance, etc. sitting on their briefcases, lurching around in the densely smoke-filled car while reading their evening paper.

One day, the regular train wasn’t working out of Westport and along comes this shiny new- looking train car. It was a private train that a lot of really rich guys owned and it had been enlisted by the New Haven Railroad to help out in the crisis. So, that day, I travelled in luxury with stewards that took your coat and hat and brushed them off. Very plush seats –the works!

One evening the train home broke down in the proverbial “middle of nowhere”. There was no train coming to save us so the whole train disgorged its riders and we all slumped along the tracks with our gear looking for some sign of humanity in the darkness. We finally came to a small house. We all camped out in the front yard while a few guys went to knock on the door to see if we could use the phone. A startled family, who were in the process of eating their supper, graciously allowed the long line of weary commuters to enter and use the wall phone. Some time later, the cars with the wives started arriving to pick us up off the front yard, one at a time.

But, I guess the oddest thing I saw on the train was one evening, very late, about 11 or so at night. I walked down the train at Grand Central to board and noticed that all the back cars were dark but I saw a little movement in them as I passed. There were people in there, in the dark! I got on in the first lighted car I found and I was only one of two people in the car. A little while into our trip, the other guy in my car asked the conductor if he was going to be opening the rear car. The conductor said he would open it in a while. Sure enough, in a while he came back and the passenger followed him to the back door where the conductor unlocked it, took something passed to him by the man and then locked it behind him.

You see, Westport is next to a city named Norwalk. A lot of girls from Norwalk would travel into New York every day to ply their “trade.” They would then ride the late train back. Sometimes they would be sitting opposite me on the train and ask to use my portfolio as a card table. I, also, had once seen a very famous game show host (I will refrain from naming him) being “entertained” by one of them in a back seat while I was in a front seat being the only other person in the car.

So… I realized what was going on the dark back cars. Some conductors evidently had a little business going. I was riding in a rolling brothel!


Randy Enos

Email Randy


Read more more of Randy’s cartooning memories:

The Pyramid of Success

The Day I Chased the Bus

The Other Ol’ Blue Eyes

8th Grade and Harold von Schmidt

Rembrandt of the Skies

The Funniest Man I’ve Ever Known

Read “I’m Your Bunny, Wanda –Part One”

Read “I’m Your Bunny, Wanda –Part Two”

Famous Artists Visit the Famous Artists School

Randy Remembers Tomi Ungerer

Randy’s Overnight Parade

The Bullpen

Famous Artists Schools

Dik Browne: Hot Golfer

Randy and the National Lampoon

Randy’s Only Great Idea

A Brief Visit to Outer Space

Enos, Love and Westport

Randy Remembers the National Cartoonists Society

By Daryl Cagle

Daryl Cagle is the publisher of and owner of Cagle Cartoons, Inc, which which is a major distributor of editorial cartoons and columns to newspapers and digital publishers. See Daryl's blog at:, see his site at: get permission to reprint his cartoons at: