Cannabis might not be a gateway to harder drugs, but alcohol prohibition was likely a gateway to recreational cannabis. In the early 20th century, many people escaped the Mexican Revolution by heading north, and some brought psychoactive cannabis with them. Prohibition took effect in 1920, and as the country went dry, some found an alternative in this "new" type of hemp that could get them high. The acceptance of cannabis was particularly prevalent within the jazz community.
The 1976 article "Songs of the Vipers" described New Orleans—the birthplace of jazz—as the "first American city where the use of marijuana took hold" and added that it was "saturated with marijuana" six years after the start of Prohibition. Around the same time, the Ku Klux Klan reached what would be its zenith, and many southern African-Americans started their own migration north. Cannabis and jazz came with them, and in the 1920s, jazz became the first genre in the U.S. to create cannabis-inspired music. That said, jazz was not the first genre overall to reference cannabis.
During the Mexican Revolution, new lyrics about smoking "marihuana" were added to the Spanish folk song "La Cucaracha," making it the first-known tune to mention smoking cannabis. In the English language, some consider the first to be Herbert Payne's "Smoke Clouds" in 1917, but the lyrics "smoke cloud, you send me dreaming" likely celebrates cigarettes, not cannabis. Within jazz music, the earliest references were instrumentals, meaning they were lit in name only, but they certainly inspired more open affection in the 1930s. Still, these Prohibition-era songs got the party started, so keep the party going with an old-school pipe packed full of Viper sativa.
1929 Trío Garnica-Ascencio - "La Marihuana"
If "La Cucaracha" was the first song to mention smoking cannabis, it's only fitting that another Spanish-language song might be the first to reference its slang name in the title. Historical records suggest Trío Garnica-Ascencio—an early Mexican group featuring Julia Garnica and sisters Ofelia and Blanca Ascencio—recorded this cannabis anthem in 1929. "La Marihuana" joins the musical tune "Sweet Marijuana" (1934) and Barney Bigard Sextet's "Sweet Marijuana Brown" (1945) as the earliest title references to marijuana/marihuana, a rare slang term prohibitionists helped popularize.
In 1929, Mississippi-born Lucille Bogan released "Pot Hound Blues," which included cannabis-friendly Tampa Red on guitar, though "pot hound" likely meant a hungry street dog that'll eat (or fuck) anything. Likewise, McKinney's Cotton Pickers possibly had cannabis in mind with "Selling That Stuff," though it's more likely that "stuff" was speakeasy whiskey. Frankie Jaxon's "Jive Man Blues" is another song that might reference cannabis, but the connection is vague and uncertain, unlike the subject of the Memphis Jug Band's "Cocaine Habit Blues."
1928 Louis Armstrong - "Muggles"
The New Orleans-born composer and trumpeter first started smoking cannabis in the mid-1920s, and his 1928 instrumental "Muggles" (a slang term for cannabis smokers) is often called the first song inspired by cannabis. Armstrong certainly elevated the subject matter with "Muggles," but it might not even be his first lit song. Two years earlier, he released "Drop That Sack" (see 1926), and maybe he should've listened to his own advice before police arrested him for cannabis possession in 1930.
1927 Frankie 'Half Pint' Jaxon - "Willie the Weeper"
"Willie the Weeper," a vaudeville standard about drug-induced fantasies, was likely written in the early 1900s and first recorded in the early 1920s. Frankie "Half Pint" Jaxon recorded his own version in 1927 that may have inspired lines in Cab Calloway's "Minnie the Moocher." Over his career, Jaxon performed with cannabis-friendly artists like Tampa Red, Bessie Smith, Ethel Waters and the Harlem Hamfats, but "Willie" likely dabbled in all drugs, not just cannabis. Victoria Spivey's "Dope Head Blues" is another cannabis-adjacent song that year, but the "dope" is likely coke and/or opium, which both seemed to thrive under Prohibition.
1926 Louis Armstrong - "Drop That Sack"
Papa Charlie Jackson's "Drop That Sack" in 1925 definitely wasn't about cannabis, and Armstrong's wife Lillian took the lead on this instrumental she recorded with Louis and the Hot Shots. That said, did the Armstrongs have cannabis sacks in mind for this song? Probably not, but Louis was an early advocate, so it's somewhat reasonable to hope they did.
1925 Original New Orleans Rhythm Kings - "Golden Leaf Strut"
Attributing lit-ness on song titles alone can be iffy, but "Golden Leaf Strut" might be the first jazz instrumental meant to reference cannabis. The all-white Rhythm Kings were essentially the Eminem of early jazz, and the band covered "Sobbin' Blues" in 1923 with Jelly Roll Morton on the piano. Just as "Golden Leaf Strut" might be the first public cannabis reference in a song title, "Sobbin' Blues" was one of the first openly interracial recordings. In the age of an ascendant KKK, the cover suggests the band didn't give a fuck, which lends more credence to the idea that these white boys blazed the golden leaf.
1924 Sidney Bechet - "Pleasure Mad"
Sidney Bechet composed "Pleasure Mad" in 1924, and Blossom Seeley, Ethel Waters and Bennie Krueger's Orchestra (whose version is heard here) all recorded the instrumental that same year. Did the New Orleans-born jazz musician use "pleasure" as a code word for cannabis high when he wrote the song? One might argue yes based on Bechet's own recording in 1938 that included a new title, "Viper Mad," and the introduction of vocals. The fully lit lyrics in '38 included, "Wrap your chops 'round this stick of tea / Blow this gage and get high with me / Good tea is my weakness, I know it's bad / It sends me gate and I can't wait, I'm viper mad." (Tea and gage are slang for cannabis, and a viper is someone who smokes it.) If Bechet did have cannabis in mind at the time he wrote it, "Pleasure Mad" would represent the start of lit music, albeit in an underground way.
Some associate Hazel Meyers' "Pipe Dream Blues" with cannabis, and the 1924 song does mention tea, but the focus of the lyrics is clearly on smoking opium. Coincidentally, opium prohibition started in 1915 with the Harrison Narcotics Tax Act, which set the precedent for tax-based prohibition, and the government utilized this approach in 1937 when it prohibited cannabis via the Marihuana Tax Act.