The first glimpses into Hogan's Alley look more like Riis's world than that of vaudeville; the initial drawings offer more social commentary and less escapism. The first official Hogan's Alley to appear in the New York World, "At the Circus in Hogan's Alley," shows a group of children improvising their own circus in the slums of New York. Many of the children are laughing, but the cartoon is about what the children don't have—and what they are trying to create instead; in some ways it does reflect a land of opportunity of sorts. Later that month "The New Restaurant in Casey's Alley" shows a group of children staring longingly at a fancy restaurant menu (oysters and poisson will be served), while "Snag McFarlin" retorts: "Dat eatin' store ain't goin' ter succeed, fer no one in dis district ever et such truck as dose—an besides, if dem tings is as hard on der stummick as dey is ter pernounce, dey'll kill surer'n Coney Island whiskey. See?" Yet the other children don't respond, as if perhaps they don't agree and long for the fancy fare. "An Untimely Death," published in the November 24, 1895 World shows two children talking about the death of a brother (who died hungry) close to Thanksgiving—hardly rich comedic material, and likely a chide toward the rich during the holiday giving season. The July 7 comic that same year shows the walking wounded after the "glorious" July 4; many children are missing arms, and "Mickey is dern near ded" according to a sign, although the Yellow Kid merely has his arm in a slang (he wasn't named Mickey Dugan until later). The December 15 "Merry Xmas Morning in Hogan's Alley" shows in one corner a little girl in a shawl with outreached arm, as if she's begging; a sign asks Santa Claus to use the ladder because the residents have no chimney, and you see an upset adult in the background door. Another child thumbs his nose at a man collecting money for foreign missions—suggesting that the money might be better spent at home. "Moving Day in Hogan's Alley," published on May 3, 1896, shows the Dugan family being defiantly evicted from their third-floor apartment (compare this to the Harper's Weekly version) and leaving in a horse-drawn buggy.
Interspersed with these more serious drawings are those that more explicitly bring the world of the rich into the world of Hogan's Alley. "Golf—the Great Society Sport as Played in Hogan's Alley" on January 5, 1896 reveals the violent consequences of allowing Hogan's Alley urchins to try their hand at golf—there are plenty of banged heads and eyes. We also see some kids trying to wear golf fashion, pointing out how ridiculous the costumes (theirs and golfers') can appear. "The Great Social Event of the Year in Shantytown," published November 10, 1895, mocks a real society wedding; (a parrot cackles, "this knocks the [real] Gool wedding silly"); children are dressed up in makeshift wedding wear, the buggy is pulled by a goat, and a bench stacked with press representatives are featured. The next week's cartoon takes it a step farther, as we see the children don fancier wear—clothes they could not own or make at home—at a Shantytown horse show. The girls' hats are ridiculously large; one sits in "McStabb's Private Box"—what looks like a packing box—and sign tells readers that prizes will be rewarded for Ade blew bludedest girl." The Kids also have a dog show (New York World, Feb. 16, 1896) and dress fancy for "Easter in Hogan's Alley" (March 22, 1896). In the latter their noses are held high, as if imitating the snobby air of the rich. The children are undercut by the signs around them: A box holding a chicken reads, "Googan's Singing Hen/She lays hand painted Easter eggs all ready hard boiled fer the trade"; a sign in the background "Prof Alec Ushun /All kinds of dramatic acting taught"; and "Prof. Cathode's new system of fortunetelling by means of the x rays/we penetrate the future and photograph the past." The first and last signs may joke at the gullibility of the poor or rich regarding fads of the day, while the dramatic acting sign points to the kids' own playacting. The Kid is presented as circus ringleader, as is often the case, spreading one arm toward the action. A June 7, 1896 cartoon shows the "First Grand Coaching Parade of the Season in Hogan's Alley"; their coaches are drawn by pigs, dogs, and goats.