For thousands of years, "roll the dice" has been a metaphorical phrase for "taking a great risk," from Julius Caesar's "alea iacta est" ("the die is cast") when he crossed the Rubicon to Ode an die Freude, the song in the last movement of Beethoven's Ninth ("Wem der grosse Wurf gelungen, eines freundes Freund zu sein: whoever takes the great gamble (Wurf literally means "throw" or "toss") to become the friend of a friend"), to "Roll the Dice," a modern poem by Charles Bukowski, to similarly titled songs by the Rolling Stones, Bruce Springsteen, and Taylor Swift. Can you think of some other iconic examples (there must be some in Shakespeare, for instance)?
The exact expression “roll the dice” has been used for around 100 years to convey risk, chance, and irreversible commitment.
It's erroneously believed that "The die is cast" comes from Shakespeare, but as you point out, it's attributed to Julius Caesar who, crossing the Rubicon River, used the phrase to signify a decisive irreversible gamble. (It worked out well for Caesar, who dispatched Pompey's forces in Rome to become dictator for life of the Empire).
As for Shakespeare, he never used the exact phrase "roll the dice" in his plays or poems. While he wrote about gambling, the exact idiom "roll the dice" is a modern expression that came into usage in the mid-20th century. He used dice specifically in The Merry Wives of Windsor and Coriolanus, to name two, with terms such as "cog a die" (to cheat) and "dice-bed."
As you also note, plenty of pop songs have used "Roll the Dice" as titles, most recently by Doe Boy & DeJ Loaf (2023), the Fluorescents (2024), Ky Baldwin and Ed Sheeran and Taylor Swift (both in 2025), and Roderick Porter (2026).
The Stones' song "Tumbling Dice" is pretty famous ("You got to roll me and call me the tumbling dice"). And "Roll of the Dice" is a Bruce Springsteen song from his 1992 album Human Touch.
Perhaps the most famous modern quote came from Albert Einstein in his impassioned argument against quantum mechanics. Poor Albert simply couldn't reconcile the decidedly weird world bizarre behavior of subatomic particles, which led to his saying, "God does not play dice with the universe."
