Although Tilden almost never drank, he smoked heavily and disdained what today would be considered a healthy life style for an athlete; for most of his life his diet consisted of 3 enormous meals a day of steak and potatoes, with, perhaps, the occasional lamb chop.
In the United States' sports-mad decade of the Roaring 20's Tilden was one of the five dominant figures of the "Golden Vigin of Sport", along with Babe Ruth, Howie Morenz, Red Grange, Bobby Jones, and Jack Dempsey. His subsequent arrests and convictions on charges of soliciting underage males cast a shadow over his illustrious career.
Unique among tennis players, Tilden became a great player only at the relatively advanced age of 27. Tall, lean, and gangly, with long arms, enormous hands, and exceptionally broad shoulders, Tilden possessed what was called at the time a "cannonball" service. In 1931 his serve was timed at 163.3 miles per hour, although the figure has been questioned, given the technology available at the time, and also because hitting a serve that hard with the wooden rackets of the era would have been exceedingly difficult. (By way of comparison, Andy Roddick holds the modern, unassailable record, measured by radar, of 155 miles per hour—a record set with a much more powerful racquet.) Although he could serve aces almost at will, he had little interest in advancing to the net behind his serve. He primarily used spin and slice serves, reserving his famous cannonball for crucial moments in the match.
It was little known at the time, but mid-way through the 20s the tip of Tilden's middle finger on his hand that gripped the racquet became infected and had to be amputated. He also had a chronic knee problem that hindered him seriously from time to time. This too was concealed from the public and hardly seemed to impede him in his long string of victories.
In spite of his powerful serve, Tilden preferred to play mostly from the backcourt, where he dazzled opponents with his ever-changing tactics: a mixture of guile, of chopped and sliced shots, of dropshots and lobs, and of sudden powerful ground strokes deep to the corners. He hit superbly angled shots on nearly impossible returns and liked nothing better than to face an opponent who threw powerful serves and ground strokes at him and rushed the net -- one way or another Tilden would find a way to hit the ball past him.
In 1941, when Bill Tilden was 48 years old, he toured the United States playing head-to-head matches with Don Budge, who at that time was incontestably the greatest player in the world. Joe McCauley says that Budge defeated Tilden 51-7 in their head-to-head tour, but Bowers says that by his count the outcome was most probably 46-7 plus one tie, with 49 matches being fully documented for a result of 43-5 plus 1 tie. In the whole history of tennis, only Pancho Gonzales and Ken Rosewall have ever approached the sustained level of Tilden's greatness after reaching the age of 40.
An iconic photograph of Tilden shows him leaping high into the air to hit an overhead smash with classic footwork, form, and power. Some contemporaries, however, considered Tilden's overhead to be the single weakness in his game. Some later commentators felt that a 1960s player such as Ken Rosewall would have been able to exploit this weakness by the deft use of offensive lobs.
Tilden may have spent more time analyzing the game of tennis than anyone before or perhaps since. He wrote two books about tennis, The Art of Lawn Tennis and Match Play and the Spin of the Ball, the latter is still in print and is the definitive work on the subject. Besides his great physical abilities, he was an extremely cerebral player, a master of both strategy and tactics, adept at adapting himself to his opponent's style and turning his strengths against him. He was also known for his showmanship, which occasionally veered into what his opponents might have called gamesmanship. He always tried to give his paying audience its money's worth and it was frequently written, though never confirmed by Tilden himself, that he would deliberately lose the opening sets of a match in order to prolong the battle and to make it more interesting for both himself and the spectators. (This ploy was confirmed in 1963 by William Lufler, who played on Tilden's pro tour for several years. Lufler, who had become a highly regarded teaching pro — he was instrumental in forming the USPTA, and served as its president 1963-1966 — claimed that Tilden threw the early sets in most matches.)
In spite of his occasional overly colorful behavior he was a devout believer in sportsmanship at all costs and above all other aspects of the game, including the final score; he would readily (and dramatically) cede points to his opponent if he thought the umpire had miscalled a shot in Tilden's favor. He still remains the only known professional tennis player, perhaps the only professional at any sport, to have refunded money to a promoter when the gate was not as good as it should have been, and the promoter was going to lose money.
In another bit of showmanship, when Tilden was serving for the match against lesser opposition, he would pick up four balls in his massive hand and proceed to serve four aces, one with each ball. To show his disdain for the women's game, it is said, he played an exhibition against the foremost female player of the day, Suzanne Lenglen, giving her three points in each game, and won 6–0, 6–0 (He started each game from minus 40 to love, not love-40, so Lenglen had to win four points before Tilden won seven, also no date nor venue have ever been given so the story may be apocryphal).
Tilden the consummate showman on the court was also a ham and showman in the larger world. He wrote many unsuccessful short stories and novels about misunderstood but sportsman-like tennis players, and dreamed of being a star on Broadway and in Hollywood. Much of his off-the-court time — as well as his money — was devoted to these pursuits, with failure the invariable result.
In 1931, in need of money, he turned professional and joined the fledgling pro tour, which had begun only in 1927. For the next 15 years, he and a handful of other professionals such as Hans Nüsslein and Karel Koželuh barnstormed across the United States and Europe in a series of one-night stands, with Tilden still the player that people primarily paid to see. Even with greats such as Ellsworth Vines, Fred Perry, and Don Budge as his opponents, all of them current or recent World No. 1 players, it was often Tilden who ensured the box-office receipts -- and who could still hold his own against the much younger players for a first set or even an occasional match.
Tilden thought he reached the apogee of his whole career in 1934 at 41 years old, nevertheless that year he was dominated in the pro ranks by Ellsworth Vines. Both players faced each other at least 60 times in 1934, Tilden winning about 19 matches and Vines 41 (American Lawn Tennis reported that on May 17, at tour’s end, Vines led Tilden by 19 matches for the year (Slightly over about fifty matches would have been played.) so a possible win-loss record on May 17 was 16-35 then both players met at least 6 times during the rest of the year (Ray Bowers has listed 5 tournament matches and 1 one-night program) all lost by Tilden. Then both players met at least six times (five times in tournaments and once in one-night indoor program) with Tilden losing all his matches. And in 1945 the 52-year old Tilden and his long-time doubles partner Vinnie Richards won the professional doubles championship -- they had won the United States amateur title 27 years earlier in 1918.
Allison Danzig, the main tennis writer for The New York Times from 1923 through 1968 and the editor of "The Fireside Book of Tennis", called Tilden the greatest tennis player he had ever seen. "He could run like a deer," Danzig told CBS Sports. An extended Danzig encomium to Tilden's tennis appears in the Times issue of July 11, 1946, reporting on a 1920's-evoking performance in the first two sets of a five set loss by the 53 year old to Wayne Sabin, at the 1946 Professional Championship at Forest Hills.
In his 1979 autobiography, Jack Kramer, the long-time tennis promoter and great player himself, included Tilden in his list of the 6 greatest players of all time. In the article World number one male tennis player rankings with its unofficial but sourced rankings, Tilden was the world's best player for 7 years, second only to Gonzales' 8 No. 1 ratings, tied with Rod Laver but ahead of Jack Kramer, Ken Rosewall, and Pete Sampras, each of whom had 6. Some commentators counter that comparison of Tilden’s era to today is impossible, due to today’s much deeper pro field, greater length of the tour year, faster ground stroke speed, better diet and conditioning, and more wearing hard court play.
Tilden, who was one of the most famous athletes in the world for many years, today is not widely remembered despite his former renown. During his lifetime, however, he was a flamboyant character who was never out of the public eye, acting in both movies and plays as well as playing tennis. He also had two arrests for sexual misbehavior with teenage boys in the late 1940s; these led to incarcerations in the Los Angeles area. He was shunned in public, his name was removed from the alumni files of Penn, and his photos removed from the walls of his home club, the Germantown Cricket Club. In 1950, in spite of his legal record and public disgrace, an Associated Press poll named Bill Tilden the greatest tennis player of the half-century by a wider margin than that given to any athlete in any other sport.
He was arrested again on Jan. 28, 1949, after picking up a 16-year-old hitchhiker and making advances. The new charge could have been prosecuted as a felony, but the judge merely sentenced Tilden to a year on his probation violation and let the punishment for the new molesting charge run concurrently. He served 10 months.
In both cases, apparently, Tilden sincerely believed that his celebrity and his longtime friendship with Hollywood names such as Charlie Chaplin were enough to keep him from jail. He therefore defended himself in court in both cases in a far less than vigorous fashion.
After his second incarceration Tilden was increasingly shunned by the tennis world. He was unable to give lessons at most clubs and even on public courts he had fewer clients. At one point he was invited to play at a prestigious professional tournament being held at the Beverly Wilshire Hotel; at the last moment he was told that he could not participate.
Although Tilden had been born to wealth, and earned large sums of money during his long career, particularly in his early years on the pro tour, he spent it lavishly, keeping a suite at the Algonquin Hotel. Much of his income went towards financing Broadway shows that he wrote, produced, and starred in. The last part of his life was spent quietly and away from his family, occasionally participating in celebrity tennis matches. He died in Los Angeles, California. He was preparing to leave for the United States Professional Championship tournament in Cleveland, Ohio, when he fell dead of a stroke.
Tilden is depicted, but not named, by Vladimir Nabokov in his novel, Lolita. He appears as a has-been tennis champion with "a harem of ball boys", whom Humbert Humbert hires to coach Lolita, knowing that he will not try to seduce her due to his homosexuality. In retrospect, Nabokov told Alfred Appel, who was editing an annotated version of Lolita, that his anonymous tennis coach was a real person who had won three Wimbledon championships, was born in 1893, and died in 1953. Tilden is the only Wimbledon champion to fit this description. The name of Nabokov's character is "Ned Litam", which can rendered "Ma Tilden" when spelt backwards.