Roberto Solis was sentenced to life in prison in 1969 for murdering an armored truck driver. He became a successful poet in prison which led multiple well known writers to petition for his release. After he was released he robbed an armored truck for $3 million and is still on the run.
Considered the greatest poet in Chinese literature, Li Bai dedicated to alcohol a good chunk of his poems and drunkeness due to his rampant alcoholism. Legend has that he drowned after drunkenly trying to embrace the moon’s reflection upon the river during a ferry-ride.
Some of his classic poems on getting hammered are on the wiki-page:
The notorious stagecoach robber Black Bart never cursed, never fired his weapon, didn’t ride a horse, and left poems after his crimes.
Abram Gannibal was a black African-born Russian nobleman in the 18th century. Sold into slavery, he was eventually freed by Peter the Great and adopted into the Emperor’s household as his godson. His great-great grandson is the celebrated author and poet Alexander Pushkin.
Tommy McHugh, who at 51 “attempted to evacuate his bowels quickly due to a knock on the toilet door,” suffered a brain hemorrhage, and unlocked a previously hidden talent for creating poetry and art.
Times were tough before the Internet. The Roman poet Virgil kept a pet housefly, and upon it’s death, he held an extremely extravagant funeral for it. He even built it a mausoleum.
Su Hui, a fourth century Chinese poet, wrote a poem in the form of a twenty-nine by twenty-nine character grid. Each line can be read forward or backwards, horizontally, vertically, or diagonally. This arrangement allows for 2,848 different readings.
There was a Canadian poet who wrote almost entirely about cheese. He is widely considered to be one of the worst poets ever.
CS Lewis and Tolkien held “you laugh you lose” competitions when reading terrible poetry.