early 14c., rollen, "turn over and over, move by rotating" (intransitive); late 14c. in the transitive sense of "move (something) by turning it over and over;" from Old French roeller "roll, wheel round" (Modern French rouler), from Medieval Latin rotulare, from Latin rotula, diminutive of rota "wheel" (see rotary). Related: Rolled; rolling.
From c. 1400 as "wrap or cover by rolling or enclosing" in something, also "wrap round and round an axis;" early 15c. as "press or level with a roller." From 1510s as "to move or travel on wheels or by means of rolling." Of sounds (such as thunder) somehow suggestive of a rolling ball, 1590s; of a drum from 1680s.
Of spoken sounds, "to utter with vibrations of the tongue," by 1846. Of eyes, from late 14c. (rolle his eyne), originally suggestive of ferocity or madness. Of a movie camera, "to start filming," from 1938. Sense of "rob a stuporous drunk" is by 1873, from the action required to get to his pockets. To roll up "gather, congregate" is from 1861, originally Australian. To roll with the punches is a metaphor from boxing (1940). To roll them bones was old slang for "play at dice" (1929). Heads will roll is a Hitlerism:
If our movement is victorious there will be a revolutionary tribunal which will punish the crimes of November 1918. Then decapitated heads will roll in the sand. 
c. 1200, rolle, "rolled-up piece of parchment or paper, scroll" (especially one inscribed with an official record), from Old French rolle "document, parchment scroll, decree" (12c.), Medieval Latin rotulus "a roll of paper" (source also of Spanish rollo, Italian rullo), from Latin rotula "small wheel," diminutive of rota "wheel" (see rotary). Dutch rol, German Rolle, Danish rulle, etc. are from French.
The meaning "a register, a list, a catalogue" is from late 14c., common from c. 1800. The general sense of "quantity of material rolled up" also is from late 14c. Specific cookery meaning "small quantity of dough which is rolled before baking" is recorded from mid-15c. The meaning "quantity of paper money" is from 1846; the sense of "quantity of (rolled) film" is from 1890.
1743, "act of rolling," from roll (v.). By 1836 as "a rolling gait or motion." From 1680s as "a rapid, uniform beating" (on a drum). The slang meaning "act of sexual intercourse" is attested from 1942 (compare roll in the hay). By 1862 as "an act of rotation." The sense of "a throw" (at dice) is attested by 1926. The colloquial expression on a roll for "enjoying a run of success" is by 1976.
"in a position above and in contact with; in such a position as to be supported by;" also noting the goal to which some action is or has been directed; "about, concerning, regarding; in a position to cover;" as an adverb, "in or into a position in contact with and supported by the top or upper part of something; in or into place; in place for use or action; into movement or action; in operation," Old English on, unstressed variant of an "in, on, into," from Proto-Germanic *ana "on" (source also of Dutch aan, German an, Gothic ana "on, upon"), from PIE root *an- (1) "on" (source also of Avestan ana "on," Greek ana "on, upon," Latin an-, Old Church Slavonic na, Lithuanian nuo "down from").
Also used in Old English in many places where we now would use in. From 16c.-18c. (and still in northern England dialect) often reduced to o'. Phrase on to "aware" is from 1877.