[2] Coogan's role in Charlie Chaplin's film The Kid (1921) made him one of the first child stars in the history of Hollywood.

[3] Coogan continued to act throughout his life, later earning renewed fame in middle age portraying Uncle Fester in the 1960s television series The Addams Family.

Charlie Chaplin discovered him in the Orpheum Theatre, a vaudeville house in Los Angeles, on the stage doing the shimmy, a then-popular dance.

The following year, Chaplin cast Coogan as the abandoned child raised by his Tramp character in the silent comedy-drama The Kid (1921).

Peanut butter, stationery, whistles, dolls, records, coins and figurines were among the Coogan-themed merchandise on sale.

[6] In May 1935, 20-year-old Coogan was the sole survivor of a car crash on the winding San Diego-Imperial Valley Highway, in eastern San Diego County that killed his father, his 19-year-old best friend, actor Trent ("Junior") Durkin,[7] their ranch foreman Charles Jones, and actor and writer Robert J. Horner.

With Coogan's father at the wheel, the car was forced off the mountain highway near Pine Valley by an oncoming vehicle and rolled down an embankment.

While a child actor, Coogan worked with Near East Relief and toured across the United States and Europe in 1924 on a "Children's Crusade" as part of his fundraising drive.

[13] Coogan soon discovered, though, that nearly the entire amount had been squandered by his mother and stepfather, Arthur Bernstein, on fur coats, diamonds and other jewelry, and expensive cars.

[14] Coogan's mother and stepfather claimed Jackie enjoyed himself and simply thought he was playing before the camera.

[18][19] Coogan appeared with then-wife Betty Grable in College Swing, a 1938 musical comedy starring George Burns, Gracie Allen, Martha Raye, and Bob Hope.

[20] In 1940, Coogan played the role of "a playboy Broadway producer" in the Society Girl program on CBS radio.

After the attack on Pearl Harbor that December, he requested a transfer to Army Air Forces as a glider pilot because of his civilian flying experience.

He flew British troops, the Chindits, under General Orde Wingate, on March 5, 1944, landing them at night in a small jungle clearing 100 miles (160 km) behind Japanese lines in the Burma Campaign.

He appeared four times on the Perry Mason series, including the role of political activist Gus Sawyer in the 1963 episode, "The Case of the Witless Witness" and TV prop man Pete Desmond in the final episode, "The Case of the Final Fadeout", in 1966.

He was a guest several times on The Red Skelton Show, appeared twice on The Brady Bunch ("The Fender Benders" and "Double Parked"), I Dream of Jeannie (as Jeannie's uncle, Suleiman – Maharaja of Basenji), Family Affair, Here's Lucy, and The Brian Keith Show, and continued to guest-star on television, including multiple appearances on The Partridge Family,[27] The Wild Wild West, Hawaii Five-O and McMillan and Wife, until his retirement in the mid-1970s.

Coogan also appeared in the first season of Barnaby Jones, in the April 1, 1973 episode titled "Sing a Song of Murder".