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Watson was a member of the Watson Family, famous in the early days of Hollywood as being a houseful of child actors. He was brother to Coy Watson Jr., Harry, Billy, Delmar, Garry, Vivian, Gloria, and Louise, all of whom acted in motion pictures. The family, known as "the first family of Hollywood", lived by the Echo Park area of Los Angeles and Bobs attended nearby Belmont High School. They were honored by the Hollywood Chamber of Commerce by placing the Watson family star on the Hollywood Walk of Fame, at 6674 Hollywood Blvd., Hollywood, California. Watson was best known for his role as "Pee Wee" in the 1938 Metro-Goldwyn-Mayer film Boys Town and its sequel Men of Boys Town (1941), both starring Spencer Tracy and Mickey Rooney. Tracy and Watson became good friends during the making of the first film, and Watson was reportedly Tracy's last visitor before his death in 1967. In 1939, Watson delivered a fine, tear-jerking performance as Pud, Lionel Barrymore's grandson, in the MGM film, On Borrowed Time. Watson later made guest appearances in many television programs, including The Twilight Zone, Lou Grant, The Beverly Hillbillies, Green Acres, and The Fugitive. In addition to working in the motion pictures business, Watson went to Claremont School of Theology to become a Methodist minister, inspired from the movie Boys Town. He retired after 30 years of serving in Burbank and La Cañada, California. He died of prostate cancer in 1999 at Laguna Beach, California.

Perry Mason: The Case of the Wicked Wives
as Judge Ezra Frank

Grand Theft Auto
as Minister

Mrs. Stone's Thing
as Bartender

Skippy the Bush Kangaroo
as Rod

The Mothers-in-Law
as Officer Bailey

First to Fight
as Sergeant Maypole

The F.B.I.
as Walsh

Green Acres

Take Her, She's Mine
as Western Union Messenger (uncredited)

The Fugitive
as Milt Plummer

What Ever Happened to Baby Jane?
as Clerk in Newspaper Department

The Lucy Show
as Calvin

The Beverly Hillbillies
as Fred Penrod

The Virginian
as Hotel Clerk

The Jim Backus Show

Pete and Gladys

The Twilight Zone
as Man at Dining Room Table (uncredited)

The Bold and the Brave
as Bob

The 20th Century Fox Hour

Hi, Buddy
as Tim Martin

Hit the Road
as Pesky

Scattergood Pulls the Strings
as Jimmy Jordan

Men of Boys Town
as Pee Wee

Dr. Kildare's Crisis
as Tommy, the Crippled Child

Dreaming Out Loud
as Jimmy

Wyoming
as Jimmy Kincaid

Blackmail
as Hank Ingram

On Borrowed Time
as Pud Northrup

Calling Dr. Kildare
as Tommy Benson (uncredited)

Dodge City
as Harry Cole

The Story of Alexander Graham Bell
as George Sanders

Kentucky
as Peter Goodwin - 1861

Young Dr. Kildare
as Little Boy (uncredited)

Boys Town
as Pee Wee

Go Chase Yourself
as Junior (uncredited)

In Old Chicago
as Bob O'Leary (as a boy)

It Happened in Hollywood
as Boy

The Great O'Malley
as Boy (uncredited)

She's Dangerous
as Boy at Airport

Pay As You Exit
as Audience

Libeled Lady
as Waif (uncredited)

Show Boat

Two-Fisted
as Jimmy's Boxing Partner

Life Begins at Forty
as Meriwhether Son

Life Begins
as Edgar, Harry’s Son (uncredited)