The latest person on the receiving end of the actor's remorseful tweets is none other than Taylor Swift.
The 27-year-old tweeted several messages to the "I Knew You Were Trouble" singer just hours after her lifted an old quote of hers on his social media page.
So what exactly did he say that caused a frenzy of Swift fans to lash out?
"I try to read as much as I can. I try to read an informative article every day to stay read up on our world issues," he tweeted on Monday.
Moments after he seemingly mocked the beloved country crooner, he wrote that he would be sending a more formal apology later on.
"I will apologize to Taylor 2mrw. Welcome to the real world!!!! Everybody wanna booooo me but I'm a fan of real pop culture. No disrespect," he wrote.
LaBeouf then followed up on Tuesday morning with the following tweet, "When I woke up from the crazy nightmare I looked in the mirror & said GROW UP SHIA I take responsibility for my actions sorry @taylorswift13."
And as if there wasn't enough controversy surrounding the young star, LaBeouf revealed in a press interview for Nymphomaniac that one of the first tests he faced in nabbing the role of Jerome was to send producers a picture of his penis.
"Lars [Von Trier] goes, 'Send him the [offer] letter. The letter was, 'Are you game?'" LaBeouf explained.
"I guess the first test was, 'Let's time how long it takes this motherf--ker to send his d--k over the Internet.' It was like 20 minutes. They were like, 'All right, kid's ready.'"