1. "Riding shotgun"
Although it might be the ideal place to ride during a road trip, riding shotgun in the Old West was a much more serious matter. Stagecoach passengers literally rode with a shotgun in their hands in order to scare off robbers to ward off would-be attackers.
2. "Highway robbery"
These days, most people would refer to being charged $10 for a cup of coffee as a highway robbery. With that being said, its original definition meant literally robbing travelers on or near a highway. It's thought that the phrase was first used way back in 1611.
3. "Paint the town red"
Painting the town red is often associated with getting glammed up before heading out for a night of drinking and dancing, but that's not what it meant back in 1837. As the story goes, the Marquis of Waterford went out for a night of drinking with some friends. They all proceeded to become quite severely intoxicated, and set about destroying property in the small English town. Things got really crazy when they stumbled upon some red paint, and literally began painting the town red. Doors, a tollgate, and a swan statue were among the victims...
4. "Pulling your leg"
You'd probably think that pulling someone's leg is just a bit of light-hearted fun, but it meant something much more sinister back in 18th and 19th-century London. Thieves would drag their victims to the ground by their legs so that they were easier to steal from.
5. "Paying through the nose"
Paying through the nose for something is never a pleasant experience, but at least your face remains intact throughout. The Vikings took paying through the nose quite literally - they used to slit someone's nose from tip to eyebrow if they refused to pay tax.
6. "Read me the riot act"
If you were ever read the riot act as a child or teenager, it might have meant being confined to your room for a few weeks without being able to watch television. In 18th-century England, however, it meant that you could face time behind bars. The Riot Act of 1715 stated that groups of 12 or more people gathered on the streets could be deemed a threat to public safety, and therefore ordered to be broken up. Refusal to disperse could also have led to arrests and forcible removals.
7. "Letting the cat out of the bag"
Nowadays, letting the cat out of the bag means spilling someone's secret, however, the phrase used to mean something completely different back in Medieval times. Back then, farmers would purchase piglets from markets, which would usually be handed over in bags. The thing is that unscrupulous dealers would swap out the pigs they were supposed to be selling for much less expensive cats. This theory is quite hotly disputed.
8. "A baker's dozen"
Back in 13th-century Britain, there was a law called the Assize of Bread and Ale. It stated that if bakers were caught selling low-quality bread or undersized portions, they could have their hands chopped off. That's why a group or set of 13 is referred to as a baker's dozen - it was a sure-fire way of them keeping their hands!
9. "Meeting a deadline"
Meeting a deadline had a very different meaning during the American Civil War than it does today. A deadline was a line inside the area where Federal prisoners were kept. If any of them attempted to cross the line, they would be shot and killed.