Homer continued to fish as he grew up; he skated and later liked music and dancing and, according to one Boston contemporary, "had the usual number of love affairs." Nobody specified how many were "usual" in Boston, but Homer, during his career, painted a great many seductive girls, all graceful, pensive and modestly inviting. He painted so many, in fact, that Henry James, in an early criticism of Homer's work, deplored his "girls in calico sun-bonnets straddling beneath a cloudless sky upon the national rail fence...suggestive of a dish of rural doughnuts and pie."
At 19 Homer was supposed to start working in a haberdashery. But about this time his father happened to read a newspaper advertisement: "Boy Wanted, to apprentice in the shop of John Bufford, lithographer." Horner took that position instead. His hours were from eight to six, six days a week, and he received no salary. Instead, his apprentice fee was $300 annually.
During these years Winslow fished at dawn in Fresh Pond before hiding his rod in the bushes and carrying his catch home for the family breakfast. Then he would take the stage to Boston. His first job for Bufford demanded a degree of professional competence. He was to draw a dozen sheet-music covers—Croquet Polka, Wheelbarrow Polka, Katy Darling, and others of the sort—for Oliver Ditson, a large music publisher. A while later Homer was given the task of depicting the 42 members of the Massachusetts Senate, hardly an assignment to inspire the fervor of a man who liked to paint pretty girls.
These drawings were rush jobs. Bufford had once done his own drawings, but now, with an artist of considerable ability and industry on hand, he limited himself to handing Homer the next order. The composer Gioacchino Rossini was reputed to be so lazy that when he was writing an opera lying in bed and an aria fell to the floor, he wrote another rather than get out of bed to pick up the first. It was otherwise with Homer. One of his fellow apprentices remembered that Homer was kept so busy that when he finished one drawing he dropped it on the floor and started the next, one of the other apprentices retrieving the sketch.
During Homer's second year Bufford magnanimously paid him $5 a week. He also reduced Homer's apprentice fee to $100. On Feb. 24, 1857, his 21st birthday, Homer quit, saying he would not be a slave to any man again. After that, he never held a regular job. For the next 15 years he was primarily a magazine illustrator. He resolutely refused to provide material about himself to biographers, but he once remarked that these years were the most interesting in his life. When he left John Bufford's he did not walk far—just down the street to the Ballou building, where he rented a studio. The building was a brand-new, imposing structure constructed with the profits from Ballou's Pictorial Drawing-Room Companion, the first large illustrated weekly in America, whose success transformed journalism. The magazine was the property of Maturin Murray Ballou, son of a famous clergyman. He became an editor at 18 to avoid going to Harvard. Subsequently, he was to be a real-estate promoter, hotel builder, world traveler, dramatist and a founder of The Boston Globe.
Ballou welcomed Homer and by July of that year the magazine was introducing the youny artist to its readers with an impressive spread of a traffic tie-up on the corner of Winter, Washington and Summer streets near the Ballou office. "The local view upon this page," said the caption, "drawn expressly for us by Mr. Winslow Homer of this city...represents one of the busiest and most brilliant spots in all Boston." The most brilliant spot in Boston, in Homer's view, included a pair of frightened horses driven by an apathetic coachman, a policeman waving his arms ineffectually, a few stray dogs, an organ grinder and his monkey, and several fashionably dressed ladies and gentlemen waiting to cross the street.
The success of Ballou's Pictorial Drawing-Room Companion had inspired a weekly not limited to drawing rooms: Frank Leslie's Illustrated Newspaper, published in New York and featuring such subjects as the turf, exploring expeditions, balloons, prizefights, billiards and murders. The success of this bold venture prompted the Harper Brothers book-publishing firm to start Harper's Weekly: A journal of Civilization. Six weeks after Winslow Homer was featured in Ballou's, his famous double-page spread of football at Harvard appeared in Harper's Weekly. Football is not supposed to have begun at Harvard until 1872, but a rough-and-tumble form of the game had long been played there, the annual encounter of the freshmen and sophomores being known as Bloody Monday. The sketches were typical of Homer's lowbrow, mock-heroic work and decidedly inappropriate for Maturin Ballou's genteel magazine. One of them focused on the leader of the sophomores—tall, determined and stern, having removed his coat for the coming struggle, though otherwise fashionably dressed, even to his top hat—facing a horde of apprehensive freshmen who appear to be doing their best to look pugnacious. That was Homer's first contribution to the journal of civilization, which was to keep him busy for the next 17 years.
After six months, Harper's had a circulation of 60,000 and was crowding Hallou's out of drawing rooms. Both magazines competed for Homer's work, but Harper's used the crowd scenes and outdoor sketches that Homer liked, whereas Ballou's idea of a lively picture was "A Boston Watering-Cart, by our artist, Mr. Homer." Most of the Homer drawings in Ballou's were portraits made from photographs, such as the Boston postmaster, the city surveyor, or "Mme. LaBorde, the prima donna."
In the fall of 1859 Homer moved to New York and rented a studio near the Harper's printing plant. Ballou's went out of business three months later. The Jan. 14, 1860 issue of Harper's featured Homer's first picture of his new city: Skating on the Ladies' Skating-Pond, Central Park. The crowded ponds were ideal for Homer's talents, animated and boisterous scenes, courtly couples gliding sedately past upended beginners—a news picture and social history combined, but still of lasting interest when Homer duplicated his illustration in a beautiful watercolor. This was a pioneering work that inspired innumerable Currier & Ives lithographs.
Now 23, Homer was reserved, amiable and polite. He never talked about art and once said that a painter should not look at pictures; the rarest thing was finding an artist who knew a good thing when he saw it.