Skull and crossbones in the context of Skull and crossbones (Spanish cemetery)

The Jolly Roger was the ensign flown by a pirate ship preceding or during an attack, during the early 18th century (the latter part of the Golden Age of Piracy). The vast majority of such flags flew the motif of a human skull, or “Death's Head”, often accompanied by other elements, on a black field, sometimes called the "Death's Head flag" or just the "black flag".

The flag most commonly identified as the Jolly Roger today – the skull and crossbones symbol on a black flag – was used during the 1710s by a number of pirate captains, including Samuel Bellamy, Edward England, and John Taylor. It became the most commonly used pirate flag during the 1720s, although other designs were also in use.

Totenkopf (German: [ˈtoːtn̩ˌkɔpf], literally "dead person's head") is a German compound word for death's head. The word is often used to denote a figurative, graphic or sculptural symbol, common in Western culture, consisting of the representation of a human skull – usually frontal, more rarely in profile with or without the mandible. In some cases, other human skeletal parts may be added, often including two crossed long bones (femurs) depicted below or behind the skull (when it may be referred to in English as a "skull and crossbones"). The human skull is an internationally used symbol for death, the defiance of death, danger, or the dead, as well as piracy or toxicity.

In English, the term Totenkopf is commonly associated with 19th- and 20th-century German militarism, particularly in Nazi Germany.