Broken Hearted

Broken Hearted
After their whirlwind romance and engagement, Davidson and Grande soon began experiencing problems in their relationship, and in October 2018 they confirmed that their engagement had been called off. Shortly before this news, Grande’s ex Mac Miller was tragically found dead.

And many people attributed the breakup to the pain and heartache this had caused them both, eventually tearing them apart. Though they were no longer engaged, it was clear that the two stars still held each other in their hearts, with Grande even paying tribute to Davidson in her song “Thank U, Next”.

No Laughing Matter

No Laughing Matter

Shortly after his breakup from Grande, Davidson was taking part in a live comedy show when a fan broached a subject that was clearly off-limits to the controversial comic. When someone shouted out a joke about the death of Mac Miller, Davidson stopped the show instantly and rebuked the fan for making such a terrible comment.

Even though Davidson had made a career out of finding levity in dark moments, it was clear that this was one area that he was still struggling to process. And he would later reveal just how dark the true extent of his struggles had become.

Social Scars

Social Scars

After this traumatic incident, fans became even more concerned for Davidson’s state of mind and safety when he expressed some dark and disturbing thoughts on his Instagram channel. Not long after the post, he deleted his entire account, causing many of his fans and followers – including his ex Ariana Grande – to reach out in concern.

He ended up receiving a visit from the New York Police Department to check on his safety, as people had become so worried. In typical Davidson style, he later joked about the incident on his next appearance on Saturday Night Live.

On the Up

On the Up
Even though Davidson had clearly been going through some difficult personal times, in terms of his career, things were only getting better and better. In 2019 he announced his comedy tour with John Mulaney, who had starred with him on both Saturday Night Live and The Tonight Show Starring Jimmy Fallon.

And in fact, many critics hailed Davidson’s success as not being despite his struggles, but actually because of them. The Washington Post described Davidson as one of SNLs best ever comedians, and attributed this to his ability to draw on his own, often difficult, life experiences.

Hollywood Calling

Hollywood Calling

As well as his super successful career in stand-up and comedy sketch shows, Davidson also began to build a name for himself as a film and TV actor. In addition to collaborating with rapper Machine Gun Kelly to write a sketch for his album Hotel Diablo.

Davidson appeared in a string of hit movies in 2019, such as Jason Orley’s Big Time Adolescence, Adam Shankman’s What Men Want, Jeff Tremaine’s The Dirt, Thurop Van Orman’s The Angry Birds Movie 2, and John Turturro’s The Big Lebowski spin-off The Jesus Rolls.

Pushing Boundaries

Pushing Boundaries

As we have seen, one of the key elements to Davidson’s mega success in the world of comedy and movies, was the fact that he drew on his own life experiences and personal struggles to create hilarious, if sometimes controversial, material.

Davidson did not hold back from discussing difficult subjects, which made him very relatable to his fans and critics. However, not everyone was so pleased with his controversial or shocking jokes – and in fact, it would eventually get him into a lot of trouble.