What went wrong?' Brad Pitt playfully roasts Rihanna with awkward introduction at her Diamond Ball charity gala

He was bestowed with the honour of introducing Rihanna at her first annual Diamond Ball charity gala.

So instead of plying her with compliments, Brad Pitt made his speech really memorable by poking fun of the singer with an awkward 'intervention.'

The 50-year-old rattled off a series of tongue-in-cheek jabs that took RiRi to task for her 'disappointing' resume in hopes of helping 'this young lady find direction and purpose.'

Having a laugh: While at the Diamond Ball on Thursday, Brad Pitt introduced Rihanna with an awkward speech that jokingly mocked her accomplishments

Brad started out the introduction by flashing a childhood photo of Rihanna in Barbados and then began mocking the pop diva's rise in the music business.

'I've often asked the very questions you yourself are asking right now—what the f*** went wrong?,' the Fury star said.

'It's not a pretty story. Like so many others, Rihanna landed on the unforgiving streets of New York at the young age of 16, and soon fell in with a bad crowd, a bad crowd led by the dubious nefarious character known as the Jay Z

'For those of you not in the know, the Jay Z was an evil impresario known for churning out hit records, and ripping insane lyrics and fresh beats. '

She was in on it: The talented singer took the tongue-in-cheek jabs all in stride and came out to perform a medley of her hits dressed in a gorgeous navy Zac Posen gown and sparkling diamond necklace

Family affair: The Pour It Up singer's proud parents turned up to lend their support

The handsome Oscar winner continued his faux disdain by listing off a laundry list of her stellar accomplishments but with a sarcastic tone.

'Since turning the ripe age of 26, Rihanna sadly has had only 13 number one singles, only 54 million albums sold, only seven Grammys, 11 Billboard Awards,' he said.

Then taking aim at her various endeavors, Brad continued: 'Her resume's even more disappointing: executive producer, fashion designer, actress, entrepreneur, philanthropist, and uh, something else… and uh, she sometimes sings.'

He then pleaded with the crowd to help intervene in order to get her back on the right track.

Philanthropy: The gala was in support of The Clara Lionel Foundation, a philanthropic organization, which was founded in 2012 by the singer in honor of her grandparents, Clara and Lionel Braithwaite 

'I ask that we stand together by her side and show her our support and our love and say to her the hard words, "Rihanna, put down that sandwich, get off your ass, and do something. Goddamn it, just do something with your life.'"

Rihanna took the joke all in stride and came out to perform a medley of her hits dressed in a gorgeous navy Zac Posen gown and sparkling diamond necklace.

The gala was in support of The Clara Lionel Foundation, a philanthropic organization, which was founded in 2012 by the singer in honor of her grandparents, Clara and Lionel Braithwaite.

According to the foundation, its mission is to 'promote initiatives of health, education, arts and culture on a global scale'.