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In 1917, Valentino joined an operetta company that traveled to Utah where it disbanded. He then joined an Al Jolson production of Robinson Crusoe Jr., travelling to Los Angeles. By fall, he was in San Francisco with a bit part in a theatrical production of Nobody Home. While in town, Valentino met actor Norman Kerry, who convinced him to try a career in cinema, still in the silent film era.

Valentino, with Kerry as a roommate, moved back to Los Angeles and took up residence at the Alexandria Hotel. He continued dancing, building up a following which included older female clientele who would let him borrow their luxury cars.

With his dancing success, Valentino found a room of his own on Sunset Blvd and began actively seeking screen roles. His first part was as an extra in the film Alimony, moving on to small parts in several films. Despite his best efforts he was typically cast as a "heavy" (villain) or gangster. At the time, the major male star was Douglas Fairbanks, with a fair complexion, light eyes, and an All American look, with Valentino the opposite, eventually supplanting Sessue Hayakawa as Hollywood's most popular "exotic" male lead.

By 1919, he had carved out a career in bit parts. It was a bit part as a "cabaret parasite" in the drama The Eyes of Youth that caught the attention of screenwriter June Mathis, who thought he would be perfect for her next movie.


Displeased with playing "heavies", Valentino briefly entertained the idea of returning to New York permanently. He returned for a visit in 1917 staying with friends in Greenwich Village. It was here he met Paul Ivano; someone who would help his career greatly.

While traveling to Palm Springs, Florida to film Stolen Moments, Valentino read the novel The Four Horsemen of the Apocalypse by Vicente Blasco Ibáñez. Seeking out a trade paper, he discovered that Metro had bought the film rights to the story. In New York, he sought out Metro's Office; only to find June Mathis had been trying to find him. She cast him in the role of Julio Desnoyers. For director, Mathis had chosen Rex Ingram, with whom Valentino did not get along, leading Mathis to play the role of peace keeper between the two.

The Four Horsemen of the Apocalypse was released in 1921, becoming a commercial and critical success. It was one of the first films to make $1,000,000 at the box office, as well as the 6th best selling silent film ever.

Metro Pictures seemed unwilling to acknowledge it had made a star. Most likely due to Rex Ingram's lack of faith in him, the studio refused to give him a raise beyond the $350 a week he had made for Four Horsemen. For his follow up film, they forced him into bit part in a B film called Uncharted Seas. It was on this film that Valentino met his second wife, Natacha Rambova.

Rambova, Mathis, Ivano, and Valentino began work on the Alla Nazimova film Camille. Valentino was cast in the role of Armand, Nazimova's love interest. The film, mostly under the control of Rambova and Nazimova, was considered too avant garde by critics and the public.

Valentino's final film for Metro was the Mathis penned The Conquering Power. The film received critical acclaim and did well at the box office. After the film's release, Valentino made a trip to New York where he met with several French producers. Yearning for Europe, better pay, and more respect, Valentino returned and promptly quit Metro.

After quitting Metro, Valentino took up with Famous Players-Lasky, a studio for films that were more commercially focused. Mathis soon joined him, angering both Ivano and Rambova.

Jesse Lasky intended to capitalize on the star of Valentino, and cast him in a role that would solidify his reputation as the "Latin Lover". In The Sheik. Valentino played the starring role as Sheik Ahmed Ben Hassan. The film was a major success and would go on to define not only his career but his image and legacy. Valentino tried to distance the character from a stereotypical portrayal of an Arab man. Asked if Lady Diana (his love interest) would have fallen for a 'savage' in real life Valentino replied, "People are not savages because they have dark skins. The Arabian civilization is one of the oldest in the world...the Arabs are dignified and keen brained."

Famous Players produced four more feature length films over the next 15 months. His leading role in Moran of Lady Letty was of a typical Douglas Fairbanks nature, however the bankability of his perceived led to his character being given a Spanish name and ancestry. The film received mixed reviews but was still a hit with audiences.

In November 1921, Valentino was set to star alongside Gloria Swanson in Beyond the Rocks. The film contained lavish sets and extravagant costumes, though Photoplay magazine said the film was "a little unreal and hectic". Released in 1922, the film was a critical disappointment. Years after its release, Beyond the Rocks was thought to be lost, save for a one minute portion.[20] In 2002, the film was discovered by the Netherlands Film Museum. The restored version was released on DVD in 2006.

In 1922, Valentino began work on another Mathis penned film, Blood and Sand. Co-starring Lila Lee and Nita Naldi, Valentino played the lead, bullfighter Juan Gallardo. Initially believing the film would be shot in Spain, Valentino was upset to learn that the studio planned on shooting on a Hollywood back lot. He was further irritated by changes in production, including a director of whom he did not approve.

After finishing the film, Valentino married Rambova, which led to a bigamy trial. The trial was a sensation and the pair was forced to have their marriage annulled and separated for a year. Despite the trial, the film was still a success, with critics calling it a masterpiece on par with Broken Blossoms and Four Horsemen. Blood and Sand went on to become one of the top 4 grossing movies of 1922, breaking attendance records, and grossing $37,400 at the Rivoli Theatre alone. Valentino would consider this one of his best films.

During his forced break from Rambova; the pair began working (separately) on the Mathis penned The Young Rajah. Only fragments of this film, recovered in 2005, still remain.The film did not live up to expectations and underperformed at the box office. Valentino felt he had underperformed in the film, being upset over his separation with Rambova. Missing Rambova, Valentino returned to New York after the release of The Young Rajah. They were spotted and followed by reporters constantly. During this time Valentino began to contemplate not returning to Famous Players, although Jesse Lasky already had his next picture, The Spanish Cavalier, in preparation. After speaking with Rambova and his lawyer Arthur Butler Graham, Valentino declared a 'One man Strike' against Famous Players.

Valentino's reasons for striking were financially based. At the time of his lawsuit against the studio, Valentino was earning $1,250 per week, with an increase to $3,000 after three years. This was $7,000 per week less than what Mary Pickford made in 1916.He was also upset over the broken promise of filming Blood and Sand in Spain, and the failure to shoot the next proposed film in either Spain or at least New York. Valentino had hoped while filming in Europe he could see his family; whom he hadn’t seen in ten years.

In September 1922, he refused to accept paychecks from Famous Players until the dispute was solved, although he owed them money he had spent to pay off Jean Acker. Angered, Famous Players in turn filed suit against him.

Valentino did not back down, and Famous Players realized how much they stood to lose. In trouble after shelving Fatty Arbuckle pictures, the studio tried to settle by upping his salary from $1,250 to $7,000 a week. Variety erroneously announced it as a 'new contract' before news of the lawsuit broke. Valentino, ever prideful, threw the offer back in their faces.

Valentino went on to claim that artistic control was more of an issue than the money. He wrote an open letter to Photoplay, entitled "Open Letter to the American Public", where he argued his case, although the average American had trouble sympathizing, as most made $2,000 a year. Famous Players made their own public statements deeming him more trouble than he was worth (the divorce, bigamy trials, debts) and that he was temperamental, almost diva-like. They claimed to have done all they could and that they had made him a real star.

Other studios began courting Valentino. Joseph Schenck was interested in casting him opposite his wife, Norma Talmadge, in a version of Romeo and Juliet. June Mathis had moved to Goldwyn Pictures where she was in charge of the Ben-Hur project, and interested in casting Valentino in the film. However, Famous Players exercised their option to extend his contract, preventing him from accepting any employment other than with the studio. By this point Valentino was around $80,000 in debt. Valentino filed an appeal, a portion of which was granted. Although he was still not allowed to work as an actor, he could accept other types of employment.

In late 1922, Valentino met George Ullman, who would soon become Valentino's manager. Ullman had previously had worked with Mineralava Beauty Clay Company, and convinced them that Valentino would be perfect as a spokesman with his legions of female fans.

The tour was a tremendous success with Valentino and Rambova performing in 88 cities in the United States and Canada. In addition to the tour, Valentino also sponsored Mineralava beauty products and judged Mineralava sponsored beauty contests.One beauty contest was filmed by a young David O. Selznick entitled Rudolph Valentino and His 88 Beauties.

When Valentino returned to the United States, it was to an offer from Ritz-Carlton Pictures (working through Famous Players), which included $7,500 a week, creative control, and filming in New York.[28] Rambova negotiated a two picture deal with Famous Players and four pictures for Ritz Carlton.[29] He accepted, turning down an offer to film an Italian production of Quo Vadis in Italy.

The first film under the new contract was Monsieur Beaucaire, wherein Valentino played the lead, Duke of Chartres. The film did poorly and American audiences found it 'effeminate'.The failure of the film, under Rambova's control, is often seen as proof of Rambova's controlling nature and would later be cause to bar her from Valentino sets.Valentino made one final movie for Famous Players. In 1924 he starred in The Sainted Devil, now one of his lost films. It had lavish costumes but apparently a weak story. It opened to strong sales but soon dropped off in attendance and ended up as another disappointment.

With his contract fulfilled, Valentino was released from Famous Players but still obligated to Ritz-Carlton for four films. Valentino's next film was a pet project entitled The Hooded Falcon. The production was beset with problems from the start, beginning with the script written by June Mathis. The Valentinos were dissatisfied with Mathis' version and requested that it be rewritten.Mathis took it as a great insult and did not speak to Valentino for almost two years.While Rambova worked designing costumes and rewriting the script for Falcon, Valentino was persuaded to film Cobra with Nita Naldi. Valentino agreed only on condition that it not be released until after The Hooded Falcon debuted.

After filming Cobra, the cast of The Hooded Falcon sailed for France to be fitted for costumes. After three months they headed back to the States where a sensation was caused by Valentino's new beard which he had grown for the film.The crew and cast headed for Hollywood to begin preparations for the film, but much of the budget was taken up during pre-production.[35]Due to the Valentinos' lavish spending on costumes and sets, Ritz-Carlton terminated the deal with the couple, effectively terminating Valentino's contract with Ritz-Carlton.

During the filming of Monsieur Beaucaire, both Charlie Chaplin and Douglas Fairbanks approached Valentino privately, due to his contract with Ritz Carlton, about joining with United Artists.[29] Valentino's contract with United Artists provided $10,000 a week for only three pictures a year, plus a percentage of his films. The contract excluded Rambova from production of his films and the film set. Valentino's acceptance of the terms caused a major rift in his marriage to Rambova. George Ullman, who had negotiated the contract with United Artists, offered Rambova $30,000 to finance a film of her own. It became her one and only film, titled What Price Beauty? and starred Myrna Loy.

Valentino chose his first UA project, The Eagle. With the marriage under strain, Valentino began shooting and Rambova announced that she needed a "marital vacation".[38] During the filming of The Eagle, rumors of an affair with co-star Vilma Bánky were reported and ultimately denied by both Bánky and Valentino.The film opened to positive reviews but a moderate box office.[39]

For the film's release, Valentino travelled to London, staying both there and in France, spending money with abandon while his divorce took place. It would some time before he made another film, The Son of the Sheik, despite his hatred of the sheik image. The film began shooting in February 1926, with Valentino given his choice of director, and pairing him again with Vilma Banky. The film used the authentic costumes he bought abroad and allowed him to play a dual role. Valentino was ill during production, but needed the money to pay his many debts. The film opened on July 8, 1926 to great fanfare. During the premiere, Valentino was reconciled with Mathis; the two hadn’t spoken in almost two years.

Dating back to the de Saulle trial in New York, during which his masculinity had been questioned in print, Valentino had been very sensitive with his public perception. Women loved him and thought him the epitome of romance. However, American men were less impressed, walking out of his movies in disgust. With the Fairbanks type being the epitome of manhood, Valentino was seen as a threat to the All American man. One man asked in a street interview what he thought of Valentino in 1922 replied, "Many men desire to be another Douglas Fairbanks. But Valentino? I wonder..." Women in the same interview found Valentino, "triumphantly seductive. Puts the love-making of the average husband or sweetheart into discard as tame, flat, and unimpassioned."Men may have wanted to act like Fairbanks, but they copied Valentino's look. A man with perfectly greased back hair was called a "Vaselino".

Some journalists were still calling his masculinity into question, going on at length about his pomaded hair, his dandyish clothing, his treatment of women, his views on women, and whether he was effeminate or not. Valentino hated these stories and was known to carry the clippings of them around and criticize them.

In July 1926, The Chicago Tribune reported that a vending machine dispensing pink talcum powder had appeared in an upscale hotel washroom. An editorial that followed used the story to protest the feminization of American men, and blamed the talcum powder on Valentino and his films. The piece infuriated Valentino and he challenged the writer to a duel and then a boxing match. Neither challenge was answered. Shortly afterward, Valentino met with journalist H.L. Mencken for advice on how best to deal with the incident. Mencken advised Valentino to "let the dreadful farce roll along to exhaustion", but Valentino insisted the editorial was "infamous." Mencken found Valentino to be likable and gentlemanly and wrote sympathetically of him in an article published in the Baltimore Sun a week after Valentino's death:
“ It was not that trifling Chicago episode that was riding him; it was the whole grotesque futility of his life. Had he achieved, out of nothing, a vast and dizzy success? Then that success was hollow as well as vast — a colossal and preposterous nothing. Was he acclaimed by yelling multitudes? Then every time the multitudes yelled he felt himself blushing inside... The thing, at the start, must have only bewildered him, but in those last days, unless I am a worse psychologist than even the professors of psychology, it was revolting him. Worse, it was making him afraid...

Here was a young man who was living daily the dream of millions of other men. Here was one who was catnip to women. Here was one who had wealth and fame. And here was one who was very unhappy.
”

After Valentino challenged the Tribune's anonymous writer to a boxing match, the New York Evening Journal boxing writer, Frank O'Neill, volunteered to fight in his place. Valentino won the bout which took place on the roof of New York's Ambassador Hotel.

Boxing heavyweight champion Jack Dempsey, who trained Valentino and other Hollywood notables of the era in the art of boxing, said of him "He was the most virile and masculine of men. The women were like flies to a honeypot. He could never shake them off, anywhere he went. What a lovely, lucky guy."

Rudolph Valentino