Rudy Vallee had an amazing career, especially when you consider that he was, in many ways, the Justin Bieber of the 1920s. At least, regarding his appeal as a singer. He had a degree from Yale University when he fronted his own band, The Connecticut Yankees. He played the saxophone and by some accounts started singing reluctantly, often doing it through a megaphone, which became his trademark. (My memory of Vallee, the singer, came from a song called, "My Time Is Your Time," though I don't recall listening to it beyond the opening phrase, which was the title.)

Some credit him with being the first pop star, and if he was, then he also may have been the most intelligent pop star for the way he adjusted a career that kept changing, but always moving forward. He became a radio star, went into movies, became a character actor specializing in roles that made him the butt of jokes and the loser in any competition for the leading lady.

He had an enormous Broadway hit in the 1960s, "How to Succeed in Business Without Really Trying," and was featured in the 1967 movie version. He did a lot of television, including four appearances on "Batman" as Lord Marmaduke Ffogg.

While very good at playing the buffoon, Vallee had a temper and wasn't afraid to display it. During the prolonged divorce that ended the marriage that unravels through the stories that follow, Vallee took a swing at his wife's lawyer — and missed.

Vallee also was a notorious penny-pincher and reportedly was not popular with those who worked for him over the year. While bright in many ways, Vallee was a slow-learner when it came to marriage.

His first wife was Leonie Cauchois, in 1928. That marriage was annulled. His second marriage, to a beautiful would-be actress named Fay Webb, also was in trouble early, briefly rebounded, then, for all practical purposes, ended three years before it they divorced.

Vallee waited seven years after the divorce before he married actress Jane Greer on December 2, 1943. They were divorced seven months later. However, marriage number four, to Eleanor Norris, continued from September 3, 1949 until his death on July 3, 1986.

But return with us now to 1933 when Rudy Vallee and Fay Webb generated more stories than Brad and Angelina:

Syracuse Journal, March 16
SANTA MONICA, California (INS) — Mrs. Rudy Vallee, wife of the noted “crooner,” is en route east to rejoin her husband after a two months’ visit here with her parents, Chief of Police Clarence Webb of Santa Monica and Mrs. Webb, it was learned today.

Mrs. Vallee boarded the Santa Fe Chief Tuesday night. Her departure effectively disposes of the last rumors of discord in her romance with Rudy, rumors which have recurred ever since their near breakup last year.


Syracuse Journal, April 6
NEW YORK (Universal) — All is over now between Rudy Vallee and his wife.

The announcement was made public today, following last night’s family conference at the office of Rudy’s attorney, Hyman Bushell.

Mrs. Vallee with her father, Clarence Webb, chief of police in Santa Monica, California, will leave today by train for California.

Said Mrs. Vallee, “If by any chance there is to be a divorce — and I am not saying there will be one — proceedings will be started in my native state of California — not in Reno. I was in Reno once and I think that was enough. I’m going to remain in California the rest of my life — I think.”

Said Vallee, “I certainly will not institute any divorce action against Mrs. Vallee. If there is a divorce she can ask for it. I’m looking for a smaller place to live. I want to remain in New York City if I can find a nice, home-like place with a huge fireplace and other things I like. If I can’t, I may go to a house in the country.”


Syracuse Journal, August 21
BRIDGEVILLE, Delaware (INS) — Rudy Vallee, famed crooner and orchestra leader, narrowly escaped death today when the automobile in which he was riding overturned after skidding on a wet road during a heavy rainstorm.

Alice Faye, specialty singer with his orchestra, was badly cut and bruised, requiring medical treatment after being brought to a physician’s office by Vallee and members of the orchestra. The party later continued to Virginia Beach to fill an engagement.

Alice Faye was only a year away from beginning a very successful movie career. She'd also find herself in the middle when Vallee and his wife wound up in divorce court.

The relationship between Rudy Vallee and Fay Webb became increasingly bitter through legal battles concerning their property settlement and their divorce. That she had willingly signed the financial arrangement prevented her from changing it, though she had been quick to realize what a mistake she had made. Unfortunately for her, she happened to marry one of the shrewdest entertainers of his time, and man who knew not only how to make money, but how to keep it.

Their divorce wasn't finalized until May, 1936. Tragically, Fay Webb only had six months to live, dying on November 19 of complications from a surgical procedure. She was only 29.

Vallee, soon out of favor as a crooner, carved out a long and successful career in films and on stage, almost always playing characters that reflected and often poked fun at his image of a Yale-educated snob who existed in a world all his own. He died in 1986.

Alice Faye always denied she had a romance with Vallee. She later married another band leader, Phil Harris, and walked away from movies while she was rather young, though she worked occasionally until 1980. Her fame was kept alive on radio's "The Jack Benny Show," through the comedian's jokes directed at Harris, who was regularly featured. Alice Faye maintained a reputation as one of the nicest, best-liked people in Hollywood. She died in 1998.