The Greatest App of All Time Day 20: Venmo vs. Twitter

If you’re just tuning in, you can read all about our selection criteria for this historic contest right here. Check out the full bracket of contestants embedded below. And as always, if you think we missed your personal favorite app of all time, yell at us in the comments. Now, let’s get into today’s contestants.

Our bracket wouldn’t be complete without an app for sending money but it was tough to choose between Cash App and Venmo. The former has more viral name recognition and has been name-dropped in hip hop lyrics for years. But Venmo has been in the game longer and has more users so it ultimately triumphed.

There isn’t a whole lot to say about Venmo, it lets you send money to people you know and that turned out to be very convenient. Its biggest innovation was turning the act of sending money into content for its social feed. Anyone who’s used it knows it can be fascinating to snoop on what payments your friends are sending although that has gotten them into trouble with the FTC over privacy concerns in the past.

Let’s make one thing clear, our first nominee is Twitter, not X. So if you’re hesitant to give a thumbs up to Elon Musk’s app, your conscience can be clear. Likewise, if you want to lick Elon’s boots with your vote, you’re out of luck. We’re talking about the bird app here.

After 17 years, we don’t really know how many current users X has but it has reached as many as 500 million monthly active users, and at various times in history, it could’ve reasonably been called the most important app in the world. What started as a place to tweet about what you’re eating for lunch grew into a reliable firehose of real-time news (and fake news). Some of the strangest characters on the internet dedicated their time to posting simply for the love of the game. And the Arab Spring briefly convinced many that Twitter was capable of toppling despotic governments. By the time Donald Trump became the Tweeter-in-Chief, it started to look like the app may be just as capable of propping up despots.

While other social platforms were in a race to stuff their apps with as many features as possible, the beauty of Twitter was how little it changed. It gave users 140 characters to express themselves, and that’s about it. In 2017, that number increased to 280 characters and people thought the sky was falling but the extra digits arguably improved the experience. Experiments with live video and audio floundered, but the simple tweet remained powerful.

It wasn’t all great. Like every other social platform, Twitter has screwed up when it comes to privacy, security, harassment, misinformation, censorship, and the exploitation of children. There’s certainly a very good argument to be made that Twitter was always a very bad app. People have made that argument every day since Elon’s takeover. And while the quality of the app has declined since Twitter died, X remains the best place online to get yourself canceled.