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April 25, 2017

Lawyers and Social Media: Hilarious Tweets from the Twitter Legal Community

Trigger Warning: These tweets are loaded with sarcasm, snark, condescension, arrogance and bad attitude, but I still think they are funny.

funny lawyers on social media

I follow lawyers on social networks, particularly Twitter, for three reasons.

  1. I learn quite a bit about how to view the issues of the world through the lens of a person who understands the law.
  2. I learn quite a bit about how lawyers think, generally, about the state of most things.
  3. Some of the lawyers I follow are beyond hilarious.

I warn you, my sense of humor is a bit on the twisted side. I see funny where most people see a jack-ass or at a minimum someone who is a big fat meanie.

The tweets I found humorous are combining a number of factors including but not limited to:

  • Context
  • Perceived Intent
  • The BS Factor
  • The hopeless response from the “victim”

Funniest Lawyer 

This weeks funniest tweets come from a lawyer out of Alabama named Keith Lee. Someone retweeted an article Keith wrote for Above the Law. The article in question was basically Keiths response to the legal tech industries lack of understanding of the actual legal industry, particularly throwing under the bus a product called Stampery.

Apparently Stampery didn’t find the article all that helpful, and in fact, kinda accused Keith of not having a clue, to which Keith, in one fell Tweet, gave the person tweeting for Stampery a lesson in business planning. 

What made me laugh is how direct and in such a few amount of words Keith was able to get his point across while at the same time expressing complete disdain for the entire business model of Stampery.

Unfortunately, as I know from personal experience, the more you debate these things with guys like Keith, the more likely he will be to produce some hilarious responses to what he thinks is not a well articulated argument.

Case and point, in this tweet, Keith completely mocks the entire business of Stampery by suggesting, as a lawyer, that he would never need such a service.

Other tweets from Keith that had nothing to do with Stampery included:

Honorable Mentions

Here are a few other tweets from the lawyers on twitter who I find to be among the funniest and most entertaining. Don’t judge me for it. I wasn’t hugged enough as a child.

First, the Popehat feed is more than one dude, but they are both funny, for many reasons.


This one is so dry and sarcastic that my computer screen actually cracked like a river bed during a horrible drought.


Yes, I do like Scott even though he has sent me to the emotional emergency room on a number of occasions.

Why am I documenting what these lawyers do on Twitter?

There are a group of these lawyers who kinda hang out with each other and share the same level of disdain for humanity. They all have this in common:

  • Smart
  • Great lawyers
  • Great sense of humor
  • Zero tolerance for BS

While I do think they are funny, I also think they present a great model for what to, and not to do on social media. I think we can all learn just by watching them do their thing.

Vincent Messina
My work experience includes everything from advising businesses as a CPA, selling big business software for companies like Peoplesoft and Oracle and now, starting, running and growing a small professional services firm.
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