You need not read far into Issue #1 before you realize how utterly distant this world is from our own. Launched in the midst of the Jazz Age, the magazine assumed its readers to be bourgeois (judging from the ads), cosmopolitan, Anglo- and/or Francophile, Ivy- or private school-educated and with enough disposable income to strike the disinterested pose of the cover mascot, Eustace Tilley.

Issue No. 1, Feb. 21, 1925, opened with a section titled “Of All Things,” and these first words:
Right next door to the Follies, some young adventurer has opened a penny peep-show where you can see five hundred and fifty glorified young women for what Mr. Ziegfeld charges for his much smaller collection.
The section concluded with a manifesto by the magazine’s founder and editor-in-chief, Harold Ross, who famously proclaimed, “It has announced that it is not edited for the old lady in Dubuque.”

There is scant advertising in the slim first issues (No. 1 is just 32 pages plus cover). In an article written for the 90th anniversary issue (Feb. 23, 2015), Ian Frazier explains how it was first funded:
After returning to the States, in 1919, he (Ross) edited a short-lived version of Stars & Stripes for veterans and became a New York night-life figure known for carrying around a dummy of his still unnamed magazine and talking about it endlessly. When he finally published the first issue of The New Yorker, ninety years ago, he paid for it partly himself. Nearly half the magazine’s original funding was a twenty-one-thousand-dollar stake put up by Ross and his wife, Jane Grant, and their friend Hawley Truax. Raoul Fleischmann, a baking heir and almost millionaire whom Ross had met through mutual friends, supplied another twenty-five thousand.
Harold Ross’s involvement in World War I figured prominently in the origins of the New Yorker. It was during his time at Stars & Stripes that he met Alexander Woollcott, who was already an established New York theater critic.

At this time Ross also met Jane Grant, who was serving in the YMCA entertainment corps and was a frequent visitor to the Star & Stripes offices. Although Ross’s name looms large in most accounts of the early New Yorker, Grant played a major role in its conception and launch.
I highly recommend Thomas Kunkel’s Ross biography, Genius in Disguise, for a complete account of the magazine’s early days.
It took a few issues for the editors to sort out regular features and their order of appearance. The opening section of Issue No. 1 featured the famous Rea Irvin masthead—flanked by Eustace Tilley and the night owl—and Irvin’s distinctive typeface that would introduce “The Talk of Town” for many issues to come. However in Issue No. 1 “Of All Things” appeared under the masthead, followed by “Talk of the Town” which was (for the first and last time) under this banner:
The magazine’s second issue, Feb. 28, paired the Eustace Tilley masthead with “The Talk of the Town” for its opening section, but the March 7 issue paired it with “Behind the News” for the opening section.
With the March 14th issue, the editors decided to permanently install “The Talk of the Town” below the masthead in the lead section, relegating “Of All Things” and “Behind the News” to inside pages.
For the sake of comparison, here is the current 2015 version:
A number of short-lived regular features made their appearance in these early issues: “The Story of Manhattankind” offered drawings by Herb Roth and tongue-in-cheek accounts of early Manhattan life that featured cartoonish Indians and bumbling settlers. It is here where the magazine took its first of many shots at William Randolph Hearst, perceived rival and publisher of Cosmopolitan (more of a literary magazine in 1925, and not the sex tips and cleavage rag it is today).
The first two cartoons ever featured in the New Yorker were by Al Frueh:
“Profiles” were established at the start, the first issue featuring opera maestro Giulo Gatti-Casazza, the second issue taking aim at “Princess” Alice Roosevelt Longworth, and the third issue probing New York Times managing editor Carr Vatell Van Anda. “In Our Midst” featured local celebrity sightings and gossip, such as actress Tallulah Bankhead and writer Edna Ferber in Issue 3 (March 7).

Most of the cartoons from the very beginning were famously droll, such as this illustration by Alfred Leete…
…but a few recall an earlier style in which the action is captioned (like old Punch cartoons) in a more formal manner. The first issue featured an Ethel Plummer cartoon of an “uncle” and a “flapper” (niece or a mistress?) looking at a theater bill for The Wages of Sin:
Uncle: Poor girls, so few get their wages.
Flapper: So few get their sin, darn it!
A section titled “The Hour Glass” offered short, casual accounts of various local personalities. “Lyrics from a Pekinese” was another recurring feature by writer Arthur Gutterman, who was known for his silly poems.
Music reviews in early issues were almost entirely devoted to classical, live performances. Fritz Kreisler’s violin mastery was featured prominently in the first issue, while it wasn’t until the third issue that jazz was briefly mentioned (it was becoming “respectable” in some concert halls). It was reported that violinist Damuel Dushkin ended his performance with selections from George Gershwin’s Rhapsody in Blue.
The “Art” section featured an exhibition of British paintings at the Central Art Galleries, and a show by the Society of Independent Artists (paintings sell from 24 to 99 dollars), at the Waldorf Hotel (soon to be razed and replaced by the Empire State Building). Joseph Stella was at the Dudensing Galleries, described as a “gifted young American.”

“Motion Pictures” looked at Greed (Frank Norris’s McTeugue transferred to the screen), which was playing on the Loew Circuit; The Lost World at the Astor (“Through camera trickery, dinosaurs and other beasts of the prehistoric past live again. Interesting because it proves that the camera is a liar”); the “splendid” German-made The Last Laugh by Carl Mayer (of Dr. Caligari fame) and The Salvation Hunters by Josef Von Sternberg. The magazine called it “deadly monotonous”…”the characters just sit around and think.” German actor Emil Jannings was a favorite, and would be lauded in subsequent issues.

The first issue closed with an ad from Royal Cord Balloon Tires. Later issues would depend heavily on advertising revenue from auto manufacturers.
The early issues also featured two-page-drawings that illustrated some event described in the opening section. The Feb. 28 issue (#2), mentioned that Ciro’s opened with the Mary Hay and Clifton Webb dancing team (illustration by Reginald Marsh)…
As this was the age of Prohibition, there was a notable absence of alcohol in ads and even in print articles, although references are made to “speakeasies” and later issues would report black market prices for liquor.
The second issue’s “Talk of the Town” further elaborated on the magazine’s manifesto:
And we won’t aim to please. If we happen to please we will not apologize, but we are not in the vast army of bores struggling frantically to give people what they want.
We may not do much for the magazine world. We don’t know that we’re aiming to. But of one thing we feel quite sure: if we ever run out of things to say, just for the fun of saying them, we expect to close up this little playhouse and go to work.
The “Theatre” section of Issue No. 2 featured James Joyce’s Exiles at the Neighborhood Theatre, while a section titled “And They Do Say” featured the first (of the many subsequent references) to Eddie Cantor’s various comings and goings. It was reported Cantor left for Boston in his “Kid Boot” and that altercations between Cantor and veteran stage actress Jobyna Howland “kept 42nd Street nervous for weeks.”

Issue #2 marked the first appearance of a recurring column filler labeled “The Optimist.” It went as follows:
Pop: A man who thinks he can make it in par.
Johnny: What is an optimist, Pop?
“Books” featured a review of Ford Madox Ford’s “Some Do Not…” The reviewer Harry Este Dounce (under the nom de plume “Touchstone”) called it “as gratuitously black-biled a work of art as we ever saw.”
Under “Washington Notes” were the first of many humorous references to President Calvin Coolidge, his hayseed habits and his extreme frugality. Below, a drawing by Miguel Covarrubias (a regular contributor beginning with the first issue) in March 14 issue:
Another Covarrubias illustration in Issue # 3 (March 7) depicted journalist Heywood Broun (old Ross friend and Algonquin Round Table stalwart) hard at work on his column for the New York World:
Next Time: The Queen of Romania…