In 1892, Webb's mother, now called "Mabelle", moved to New York City with her beloved "little Webb", as she called him for the remainder of her life. She dismissed questions about her husband, Jacob, who like her father, worked for the Indianapolis-St. Louis Railroad, by saying, "We never speak of him. He didn't care for the theatre." The couple apparently divorced, since by 1900, Mabelle was married to Green B. Raum, Jr. New York City's 1900 U.S. census indicates Mabelle and her son were using the surname Raum and living on West 77th Street with Green Berry Raum, Jr., a copper-foundry worker, who gave his position in the household as Mabel's husband. Raum was the son of General Green Berry Raum, former U.S. Commissioner of Internal Revenue and former U.S. Commissioner of Pensions. Webb's father, Jacob, married, as his second wife, Ethel Brown, and died in 1939.
Webb's mainstay was the Broadway theatre. Between 1913 and 1947, the tall and slender performer who sang in a clear, gentle tenor, appeared in 23 Broadway shows, starting with major supporting roles and quickly progressing to leads. He introduced Irving Berlin's "Easter Parade" and George and Ira Gershwin's "I've Got a Crush on You" in Treasure Girl (1928); Arthur Schwartz and Howard Dietz's "I Guess I'll Have to Change My Plan" in The Little Show (1929) and "Louisiana Hayride" in Flying Colors (1932); and Irving Berlin's "Not for All the Rice in China" in the very successful revue As Thousands Cheer (1933). One of his stage sketches, performed with co-star Fred Allen, was filmed by Vitaphone as a short subject titled The Still Alarm (1930). Allen's experiences while working with Webb appear in Allen's memoirs.
The year 1917 proved to be better, with a 233-performance run of Jerome Kern's Love O' Mike, which opened at the Shubert Theatre on January 15, 1917. After moving to Maxine Elliott's Theatre and Casino Theatre, it closed on September 29, 1917. Future Mama star Peggy Wood was also in the cast. Webb's final show of the 1910s, the musical Listen Lester, had the longest run, 272 performances. It opened at the Knickerbocker Theatre on December 23, 1918, and closed in August 1919. Webb appeared with other Broadway stars in National Red Cross Pageant (1917), a 50-minute film of a stage production held to benefit the American Red Cross.
The 1920s had Webb in no fewer than eight Broadway shows, numerous other stage appearances, including vaudeville, and a handful of silent films. The revue As You Were, with additional songs by Cole Porter, opened at the Central Theatre on January 29, 1920, and closed 143 performances later on May 29, 1920. Busy with films, tours, and vaudeville, (including an appearance at the London Pavilion in 1921 as Mr. St. Louis in Fun of the Fayre and the next year in Phi-Phi), he did not return to Broadway until 1923, with the musical Jack and Jill (Globe Theatre) which had 92 performances between March 22, 1923, and June 9, 1923, and Lynn Starling's comic play Meet the Wife, which opened on November 26, 1923, and ran into the summer of 1924, closing in August. One of the play's leads was 24-year-old Humphrey Bogart.
In 1925, Webb appeared on stage in a dance act with vaudeville star and silent film Actress Mary Hay. Later that year, when her husband, Tol'able David star Richard Barthelmess and she decided to produce and star in New Toys, they chose Webb to be second lead. The film proved to be financially successful, but 19 more years passed before Webb appeared in another feature film.
Webb was born Webb Parmelee Hollenbeck in Indianapolis, Indiana. He was the only child of Jacob Grant Hollenbeck (1867 – May 2, 1939), the ticket-clerk son of a grocer from an Indiana farming family, and his wife, the former Mabel A. Parmelee (Parmalee or Parmallee; March 24, 1869 – October 17, 1960), the daughter of David Parmelee, a railroad Conductor. The couple married in Kankakee, Illinois, on January 18, 1888, and separated in 1891, shortly after their son's birth. According to Marion County, Indiana, marriage records, they married in Indianapolis on January 18, 1888.
Webb was in his mid-fifties when actor/director Otto Preminger chose him over the objections of 20th Century Fox chief Darryl F. Zanuck to play the elegant but evil radio columnist Waldo Lydecker, who is obsessed with Gene Tierney's character in the 1944 film noir Laura. Zanuck reportedly found Webb too effeminate as a person and an actor; he wanted Laird Cregar to play the role but Cregar by then was well established as an on-screen villain and Preminger wanted someone who would surprise the audience.
His first film under the contract was The Dark Corner (1946), a film noir directed by Henry Hathaway where he gave a version of his Laura performance. He was then reunited with Tierney in another highly praised role as the elitist Elliott Templeton in The Razor's Edge (1946). He received another Academy Award nomination for Best Actor in a Supporting Role.
Fox promptly put Webb in a sequel, Mr. Belvedere Goes to College (1949) where Belvedere has to complete his college degree and acts as matchmaker. It was another box office success.
Less successful at the box-office was For Heaven's Sake (1950) in which Webb played an angel trying to help a couple on earth. He made Mr. Belvedere Rings the Bell (1951), with Belvedere causing trouble in an old person's home, but the film was not as popular as the first two, resulting in the end of the series.
Around the same time, he starred in the Technicolor film biography of bandmaster John Philip Sousa, Stars and Stripes Forever (also 1952). He was a Belvedere-like scoutmaster in Mister Scoutmaster (1953). Webb had his most dramatic role as the doomed but brave husband of unfaithful Barbara Stanwyck in Titanic (also 1953). Writer Walter Reisch says this movie was created in part as a vehicle for Webb by Fox, who wanted to push Webb into more serious roles.
Soon afterwards, he played the (fictional) Novelist John Frederick Shadwell in Three Coins in the Fountain (1954), romancing Dorothy McGuire. It was a huge hit. He was top billed as a company owner in Woman's World (1954), a corporate drama.
The British film The Man Who Never Was (1956) had Webb playing the part of Royal Navy Lt. Cmdr. Ewen Montagu in the true story of Operation Mincemeat, the elaborate plan to deceive the Axis powers about the Allied invasion of Sicily during World War II. In Boy on a Dolphin (1957), second-billed to Alan Ladd, with third-billed Sophia Loren, he portrayed a wealthy sophisticate who enjoyed collecting illegally obtained Greek antiquities. In a nod to his own identity, the character's name was Victor Parmalee.
He starred in The Remarkable Mr. Pennypacker (1959), a Cheaper By the Dozen comedy as a man with two families, and Holiday for Lovers (1959), a family comedy set in South America. Neither was particularly successful. Fox were developing Journey to the Center of the Earth (1959) as a vehicle for Webb but then he fell ill and was unable to do it; James Mason took the part.
Webb never married and had no children. He lived with his mother until her death at age 91 in 1960, leading Noël Coward to remark, apropos Webb's grieving, "It must be terrible to be orphaned at 71."
Webb's final film role was an initially sarcastic, but ultimately self-sacrificing Catholic priest in Leo McCarey's Satan Never Sleeps (1962). The film, which was set in China, showed the victory of Mao Tse-tung's armies in the Chinese Civil War, which ended with his ascension to power in 1949, but was actually filmed in Britain during the summer of 1961, using sets from the film The Inn of the Sixth Happiness (1958), which had the same setting.