As many places had pianos in bad shape or none at all, Edwards taught himself to play ʻukulele to serve as his own accompanist (choosing it because it was the cheapest instrument in the music shop).

He got his first break in 1918 at the Arsonia Cafe in Chicago, Illinois, where he performed a song called "Ja-Da", written by the club's pianist, Bob Carleton.

He recorded many of the pop and novelty hits of the day, including "California, Here I Come", "Hard Hearted Hannah", "Yes Sir, That's My Baby", and "I'll See You in My Dreams".

That year he also featured in George and Ira Gershwin's first Broadway musical Lady Be Good, alongside Fred and Adele Astaire.

As a recording artist, his hits included "Paddlin’ Madeleine Home" (1925), "I Can't Give You Anything but Love" (1928), and the classic "Singin' in the Rain" (1929), which he introduced.

He also recorded a few "off-color" novelty songs for under-the-counter sales, including "I'm a Bear in a Lady's Boudoir", "Mr. Insurance Man", and "Give It to Mary with Love".

[6] In 1929, Cliff Edwards was playing at the Orpheum Theater in Los Angeles where he caught the attention of movie producer-director Irving Thalberg.

He had a small role as Mike, playing a ʻukulele very briefly at the beginning of the 1931 movie Laughing Sinners (1931), starring Joan Crawford.

Edwards was also an occasional supporting player in feature films and short subjects at Warner Bros. and RKO Radio Pictures.

He played a wisecracking sidekick to Western star George O'Brien, and he filled in for Allen Jenkins as "Goldie" opposite Tom Conway in The Falcon Strikes Back.

Throughout the 1940s he appeared in a number of "B" Westerns playing the comic, singing sidekick to the hero, seven times with Charles Starrett and six with Tim Holt.

In 1939, he voiced the off-screen wounded Confederate soldier in Gone with the Wind in a hospital scene with Vivien Leigh and Olivia de Havilland.

His most famous voice role was as Jiminy Cricket in Walt Disney's Pinocchio (1940), where he sings Give a Little Whistle and When You Wish Upon a Star.

In the early 1930s, however, Edwards' popularity faded as public taste shifted to crooners such as Russ Columbo, Rudy Vallee, and Bing Crosby.