The Five Pennies was a semi-biographical 1959 film starring Danny Kaye as cornet player and bandleader Red Nichols. Other cast members included Barbara Bel Geddes, Harry Guardino, Bob Crosby, Louis Armstrong, Susan Gordon, and Tuesday Weld. The film was directed by Melville Shavelson.

The film received four Oscar nominations: Best Musical Scoring (Leith Stevens), Best Original Song (Danny Kaye's wife Sylvia Fine), Best Cinematography (Daniel L. Fapp), and Best Costumes (Edith Head).

The real Red Nichols recorded all of Kaye's cornet playing for the film soundtrack. Unfortunately, the other musicians in Red's band were not asked to provide their musical contributions and the sound of his "band" was supplied by session players.

Red Nichols (Kaye) is a small-town cornet player who moves to New York City in the 1920s and finds work in a band led by Wil Paradise (Crosby). He meets and marries singer Bobbie Meredith (Bel Geddes), and the two form their own Dixieland band called "The Five Pennies" (a play on Nichols' name, since a nickel equals five pennies). As their popularity peaks, their young daughter Dorothy (Susan Gordon) contracts polio and the family leaves the music business, moving to Los Angeles. When Dorothy becomes a teen (Tuesday Weld) she learns of her father's music career and persuades him go on a comeback tour. The tour borders on failure until several notable musicians from Nichols' past appear to save the day.

The Five, also known as The Mighty Handful, The Mighty Five, or The Mighty Coterie (Russian: Могучая кучка, Moguchaya kuchka), refers to a circle of composers who met in Saint Petersburg, Russia, in the years 1856–1870: Mily Balakirev (the leader), César Cui, Modest Mussorgsky, Nikolai Rimsky-Korsakov and Alexander Borodin. The group had the aim of producing a specifically Russian kind of art music, rather than one that imitated older European music or relied on European-style conservatory training. In a sense, they were a branch of the Romantic Nationalist movement in Russia, sharing similar artistic goals with the Abramtsevo Colony and Russian Revival.

In May 1867 the critic Vladimir Stasov wrote an article, Mr. Balakirev's Slavic Concert, on a concert given for visiting Slav delegations to the "All-Russian Ethnographical Exhibition" in Moscow. The four Russian composers whose works were played at the concert were Mikhail Glinka, Alexander Dargomyzhsky, Mily Balakirev, and Nikolai Rimsky-Korsakov. The article ended with the following statement:

Danny Kaye (born David Daniel Kaminski; January 18, 1913 – March 3, 1987) was a celebrated American actor, singer, dancer, and comedian. His best known performances featured physical comedy, idiosyncratic pantomimes, and rapid-fire nonsense songs.

Kaye starred in 17 movies, notably The Kid from Brooklyn (1946), The Secret Life of Walter Mitty (1947), The Inspector General (1949), Hans Christian Andersen (1952), and — perhaps his most accomplished performance — The Court Jester (1956). His films were extremely popular, especially his bravura performances of patter songs and children's favorites such as The Inch Worm and The Ugly Duckling. He was the first ambassador-at-large of UNICEF in 1954 and received the French Legion of Honor in 1986 for his many years of work with the organization.

David Daniel Kaminski was born to Ukrainian Jewish immigrants in Brooklyn. Jacob and Clara Nemerovsky Kaminski and their two sons, Larry and Mac, left Ekaterinoslav two years before his birth; he was the only one of their sons born in the United States. He spent his early youth attending Public School 149 in East New York, Brooklyn, where he began entertaining his young classmates with songs and jokes, before moving to Thomas Jefferson High School, but he never graduated. His mother died when he was in his early teens. Clara enjoyed the impressions and humor of her youngest son and always had words of encouragement for them; her death was a great loss for young Danny.

Ernest Loring "Red" Nichols (May 8, 1905 – June 28, 1965) was an American jazz cornettist, composer, and jazz bandleader.

Over his long career, Nichols recorded in a wide variety of musical styles, and critic Steve Leggett describes him as "an expert cornet player, a solid improviser, and apparently a workaholic, since he is rumored to have appeared on over 4,000 recordings during the 1920s alone."

Red Nichols is a name which comes to us from the jazz of the 1920s, a time when Nichols was a fecund recording artist. But that name got a second lease on life when Hollywood made a movie, The Five Pennies, (starring Danny Kaye) very loosely based on Nichols’ life, in 1959.

Ernest Loring (“Red”) Nichols was born on May 8, 1905 in Ogden, Utah. His father was a college music professor, and Nichols was a child prodigy, because by twelve he was already playing difficult set pieces for his father’s brass band. The young Nichols heard the early recordings of the Original Dixieland Jazz Band (which was not in fact “original,” but was the first “jazz” band to record), and later those of Bix Beiderbecke, and these had a strong influence on the young cornet player. His style became polished, clean and incisive.

Louis Armstrong (August 4, 1901 – July 6, 1971), nicknamed Satchmo or Pops, was an American jazz trumpeter and singer from New Orleans, Louisiana.

Coming to prominence in the 1920s as an "inventive" cornet and trumpet player, Armstrong was a foundational influence in jazz, shifting the music's focus from collective improvisation to solo performance. With his instantly recognizable deep and distinctive gravelly voice, Armstrong was also an influential singer, demonstrating great dexterity as an improviser, bending the lyrics and melody of a song for expressive purposes. He was also greatly skilled at scat singing (vocalizing using sounds and syllables instead of actual lyrics).

Renowned for his charismatic stage presence and voice almost as much as for his trumpet-playing, Armstrong's influence extends well beyond jazz music, and by the end of his career in the 1960s, he was widely regarded as a profound influence on popular music in general. Armstrong was one of the first truly popular African-American entertainers to "cross over," whose skin-color was secondary to his music in an America that was severely racially divided. It allowed him socially acceptable access to the upper echelons of American society that were highly restricted for a black man. While he rarely publicly politicized his race, often to the dismay of fellow African-Americans, he was privately a strong supporter of the Civil Rights movement in America.^{[citation needed]}