1. "Roll up the window"
Because pretty much all cars have power windows that come standard, nobody spends much time using the manual crank to "roll up" windows anymore. Maybe it's a force of habit, but saying "roll up the window" sounds a lot better than "press the up button until the window closes."
2. "Hold your horses"
This one comes from the days when horses were the main means of transportation, so saying "hold your horses" is basically a command to not go anywhere. Today, we use it to tell someone to have some patience.
3. "Like a broken record"
Music used to be stored on vinyl records rather than digitally in clouds, but there were some inherent dangers to this physical medium. A record that was scratched or "broken" would bounce the needle back to a previous spot on the record, causing it to play the same thing over and over. When someone won't stop repeating something, this is why we say they are like a broken record.
4. "Rewind"
Once we graduated from vinyl and moved on to cassettes, a new vocabulary was required. When these devices played, the tape was pulled from one spool onto the other. If you wanted to hear or see the same part again, you would have to "rewind" the tape back onto the spool and play it again. With music and film totally digital, there's no actual winding going on, but everyone still knows what the phrase means.
5. "Don't touch that dial"
When TVs first came out, there were no remote controls or buttons to push to change the channel. Instead, channels that could be picked up over the antenna could be accessed by turning a dial to see what was available to watch. TV personalities would say "don't touch that dial" and hope people would stay on their channel, because they knew if someone had to actually get up, walk across the room, and flip through the dials to find something else to watch, there was a good chance they weren't coming back.
6. "Hang up the phone"
Back when phones couldn't travel any more than their cord would allow, you actually had to put them back onto the base which pushed down a button, ending the call.
The best part of being able to hang up a phone was getting to slam the phone down when hanging up on someone. Now we all just angrily stab the "end call" button on our iPhones, which is not nearly as satisfying.
7. "Running out of steam"
Back in the day when steam engines were all the rage, running out of steam meant running out of power. Now, the phrase gets used when someone is starting to get exhausted.
8. "Dial the number"
Just like "hanging up" our phones now, putting in a person's phone number now just involves poking the screen. Back in the days of rotary phones, someone would have to spin a dial to call a particular number.
9. "Kodak moment"
We now live in a day and age where people take roughly eleventy billion pictures every single day of basically every aspect of their lives. Back when people actually had to pay for film and pay to get pictures developed, people were more judicious of when they snapped the shutter. Photographs were saved for special moments worth remembering. Kodak (a film and camera company, to the kids at home who might not know) coined the phrase "Kodak moment" as an ad campaign to signify times worth cherishing.
10. "Drop a dime"
Before everyone and their 5-year-old nephew had a cell phone, people away from home would use a pay phone to get in touch with someone. Back in the day, these calls could be made by depositing 10 cents into the phone. Thus, to "drop a dime" means to call someone.
11. "On the flip side"
To catch someone "on the flip side" just means you'll see them later. However, this originally started as a way to describe music on the other side of the record.
12. "Been through the wringer"
Back before everyone used washers and dryers, laundry needed to be hung out to dry. The best way of extracting water from the clothes before this happened was to put it through a "wringer," which squeezed out water using two rollers. Now we say it about someone who has been through a really tough time.
13. "Nothing to write home about"
In the days when phone calls were expensive and computers didn't exist, people communicated with relatives with letters. A trivial matter that happened in someone's life that wasn't "worth writing home about." Nowadays, if something isn't worth writing home about, someone would probably still make a Facebook status about it.
14. "Jump the shark"
Although Happy Days was one of the best shows that has ever been on television, it started to grasp at straws for plot lines toward the end (as so many shows do), and not all of them were great. In once episode, The Fonz is on waterskis and jumps over a shark. It caused one of the biggest collective eye rolls in the century, and the phrase "jump the shark" is now used whenever someone has gotten too ridiculous for words.
15. "Close, but no cigar"
Carnival games are basically impossible to win today, and they were impossible in the late 19th century when this phrase came to be. Back then, instead of a cheap teddy bear whose stitching barely lasts to the end of the day, cigars were the prizes. When someone playing the game almost won but didn't (because of course they didn't) the carnival attendant would taunt, "close, but no cigar."