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Smiling Sean Penn catches night two of ex-wife Madonna's Rebel Heart Tour at Madison Square Garden

Published: 12:24 EST, 18 September 2015 | Updated: 15:14 EST, 18 September 2015

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Madonna and Sean Penn had a famously tumultuous relationship.

However, that hasn't stopped the divorced pair from remaining friends, as Sean, 55, showed on Thursday by attending the second night of Madonna's Rebel Heart Tour at Madison Square Garden in New York City.

He was spotted front and center as the 57-year-old performed True Blue during the show, as reported by TMZ.

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True Blue friendship! Sean Penn was spotted enjoying ex-wife Madonna's Rebel Heart concert at Madison Square Garden on Thursday

Sean looked laid-back as he stood enjoying his ex-wife's show in a button down, jeans, and a leather jacket.

He can be seen sporting a smile as he listens to the star - to whom he was married from 1985 to 1989 - sing her romantic, 1986 hit.

And despite their difficult past, this isn't the first time Sean has been spotted supporting his ex at one of her shows.

Supportive: Despite their tumultuous past - the pair divorced in 1989 - Sean seemed happy to support his ex at her show

Flashback: Sean and Madonna - pictured in 1988 - met on the movie lot when Madonna was filming her Material Girl video, and married in 1985

In 2012 the Oscar winner was seen sneaking out of the Staples Center in Los Angeles after catching one of the performances on Madonna's MDNA Tour.

The pair met on the movie lot when Madonna was filming her Material Girl video, when Penn was already minor Hollywood royalty.

Of the passionate relationship, Madonna has said privately that the fireworks between them were unlike anything she's ever experienced, before or since.

However, the famously toxic relationship was also fraught with Sean's criticism, mood swings, and violence.

The way they were: The couple - pictured in 1987 - had a famously toxic relationship, but Madonna has said privately that the fireworks between them were unlike anything she's ever experienced, before or since

Putting on a show: As is her style, Madonna didn't hold back during the performance, at one point twerking in a tiny, black ensemble covered in chains of dangling jewels

The worst offense occurred in December of 1989, a week after which Madonna called her lawyers and told them to file divorce papers. However, she opted to withdraw assault charges against her husband.

Despite the violent outbursts, the two never truly fell out of contact, and Sean would call Madonna frequently when she was with Warren Beatty (who was 21 years her senior) to say that he was too old for her. He called Warren often, too, to tell him to leave her alone.

They were in touch again as she attempted to revive her film career with Evita (1996), when she declared Penn to be, once again, her friend.

In fact, she welcomed him so warmly back into her life that it's said she invited him to be present at the birth of her daughter Lourdes - with Carlos Leon - in 1996.

Dressed to the nines: The Queen of Pop had a collection of eye-catching costume changes, including this shimmery, black dress, coupled with metallic pumps and a black bowler cap

Lending a hand: Backup dancers clad in tuxedos helped to carry the train of a long veil Madonna was draped in as she performed one number

And now the actor - who recently split with younger girlfriend Charlize Theron, 40 - was seen happily supporting his ex at Thursday's performance.

Madonna certainly put on quite the show for her ex, and the rest of the Madison Square Garden audience, as she flaunted her figure in revealing, skintight ensembles while dancing around the stage.

She showed off her moves while twerking in a tiny black number decorated in chains of dangling jewels, while sporting a black bowler cap.