"The Wreck of the Hesperus" is a story that presents the tragic consequences of a sea captain's pride. On an ill-fated voyage in the winter, he had his daughter aboard ship for company. The disaster came when the captain ignored the advice of one of his experienced men, who feared that a hurricane was approaching. When the hurricane arrives, he ties his daughter to the mast to prevent her from being swept overboard; she calls out to her dying father as she hears the surf beating on the shore, then prays to Christ to calm the seas. The ship crashes onto the reef of Norman's Woe and sinks; a horrified fisherman finds the daughter's body, still tied to the mast, drifting in the surf the next morning. The poem ends with a prayer that we all be spared such a fate "on the reef of Norman's Woe".

Longfellow combined fact and fancy to create this, one of his best-known, most macabre, and most enduring poems. His inspiration was the great Blizzard of 1839, which ravaged the northeast coast of the United States for 12 hours starting January 6, 1839, destroying 20 ships with a loss of 40 lives. He probably drew specifically on the destruction of the Wiscasset, Maine ship Favorite on the reef of Norman's Woe (located off the coast of Gloucester, Massachusetts); all hands were lost, one of whom was a woman, who reportedly floated to shore dead but still tied to the mast. It is possible that this detail was taken from a different ship that foundered during the same storm, however.

There is a legend that, in January 1840, Longfellow literally missed the boat, specifically a steamboat embarking upon a voyage from New York City to New England, because he had been discussing the merits of the new poem with a publisher and arrived late at the pier. The steamboat he supposedly missed was the steamship Lexington, that caught fire and sank with the loss of 139 out of 143 passengers and crew on that voyage.

Mad magazine, in its early years, parodied much poetry by presenting the text with little or no change but with bizarre illustration by a member of its art staff. Wallace Wood took Longfellow's somber poem and illustrated it in a ridiculous manner, with a pint-sized captain, and a hideous, tall, buck-toothed daughter. The ship is found wrecked the morning after the storm, but the captain and his daughter survive and walk off along the shore (she is still tied to the broken-off twenty-foot-tall massive mainmast!), and the fisherman chases after them with her wig, shouting "Norman! Whoa!"

"The Wreck of the Hesperus" is also referenced in the comic song "Lydia the Tattooed Lady," written by Harold Arlen and Yip Harburg and performed by Groucho Marx in the Marx Brothers movie At the Circus (1939). It became one of Groucho's signature tunes.

The title phrase has also been used as a colloquial term in the UK to mean a "disheveled appearance," spoken as "You look like the wreck of the Hespress!" it can also refer to a very untidy room. Its everyday use was greater in the 1950s to 1970s, however its use remains popular in more cultured circles. Former Beatle George Harrison referenced this colloquial usage in writing his song "Wreck of the Hesperus," included on his 1987 album Cloud Nine.

In The Simpsons sixth season episode "Homer the Great", Homer Simpson is repeatedly paddled by the Stonecutters as an initiation prank. Each of the paddlings is given a name, one of them being "The Wreck of the Hesperus."

In Mighty Mouse Season 1, Episode 1, "The Wreck of the Hesperus" (First Aired: February 11, 1944), Mighty Mouse rescues the crew from being eaten by sharks.

In an episode of The Odd Couple, Oscar mentions the poem casually to Felix.

In the Looney Tunes cartoon The Ducksters, (1950), Porky Pig asks Daffy Duck, "In what latitude and longitude did the wreck of the Hesperus occur?"