When Twitter first launched in 2006, it was hard to imagine it becoming the social media giant it is today. According to Twitter’s website, they currently have over 288 million monthly active users, and 500 million tweets are sent per day. Among these 288 million users are many celebrities who use the platform to connect with their adoring fans – or their haters. Like anyone else, celebrities make mistakes too. Some of these mistakes happen to be sending out embarrassing and regretful tweets, and here is a collection of twenty of the worst of them.

Chris Brown

Singer Chris Brown definitely isn’t known for being well-behaved, or for making very good decisions. When he tweeted, “I know a lot of you wack ass (OLD) celebrities probably wanna f— my ex, but talking sh-t on me wont get you far! and to be REALLY HONEST, ya’ll wonder why ni— spazzes all the time,” he still managed to surprise his followers with how low he could go. In the tweet, Brown was referencing his ex, Rihanna, who he beat up in 2009, and the tweet was deleted shortly after posting it.

MIchael Moore

Filmmaker Michael Moore has always been outspoken. When he tweeted about Clint Eastwood’s latest film, American Sniper, he sparked a lot of controversy. The film is based on real-life American Sniper, Chris Kyle, who is credited with being the most deadly sniper in US Military history, and was killed by a fellow veteran in 2013. Moore tweeted, “My uncle killed by sniper in WW2. We were taught snipers were cowards. Will shoot u in the back. Snipers aren’t heroes. And invaders r worse.” Although many liberals took Moore’s side, many right wingers were outraged.

Gilbert Gottfried

Most comedians aren’t known for being able to keep their mouths shut about sensitive topics, and Gilbert Gottfried contributed to this stereotype in 2011 with some regretful tweets. When Japan was hit with a massive and devastating tsunami, Gottfried tweeted, “Japan is really advanced. They don’t go to the beach. The beach comes to them.” Not only was the public horrified, the tweet cost Gottfried his job as the voice of the Aflac duck.

Jason Biggs

Only an hour after it was announced that Malaysian Airlines Flight 370 crashed, actor Jason Biggs took to twitter and asked, “Anyone wanna buy my Malaysian Airlines frequent flier miles?” His tweet was definitely not well-received, and he tweeted a four-part apology shortly after.

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