The love triangle involving and was arguably the biggest showbiz story of all time.
But the Fight Club actor was not the only one who shared an intimate moment with each of the A-listers.
Gerard Butler was asked who was a better kisser between Aniston and Jolie during an appearance on on Wednesday night.
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Good spirits: Gerard Butler made an appearance on Watch What Happens Live With Andy Cohen on Wednesday night - and discussed the intimacies of smooching Hollywood's leading ladies
Tough choice: He participated in a Plead The Fifth game where he was asked by the 49-year-old host who was a better kisser between Angelina Jolie (left) and Jennifer Aniston
The 48-year-old Scottish actor participated in a Plead The Fifth game where he was asked by the 49-year-old host which between the star actresses is better to smooch.
As he had already plead the fifth once, he looked pained to have to answer as he finally said: 'Jennifer Aniston. I'm just going, you know, I'm just taking you by surprise.'
Gerard could be seen with shaky legs but other guest 50 Cent seemed pleased by his answer as he smiled big and said: 'No no no this is good!'
The hunk worked with 48-year-old Aniston on 2010's Bounty Hunter and with 42-year-old Jolie in 2003's Lara Croft Tomb Raider: The Cradle of Life.
Interesting: The 48-year-old Scottish actor participated in a Plead The Fifth game where he admitted that Aniston was the better kisser
What a team: The Paisley, United Kingdom-born star worked with 48-year-old Aniston on 2010's Bounty Hunter
Intimate: Gerard worked with 42-year-old Jolie in 2003's Lara Croft Tomb Raider: The Cradle of Life
Both actresses were also famously been married to Brad Pitt; Aniston from 2000 to 2005 and Jolie from 2014 until 2016.
It's been claimed that Jolie 'stole' Pitt away from Aniston while making the movie Mr & Mrs Smith in 2005, but other reports suggest that Pitt and Aniston were already on the outs when he met Jolie.
In an interview with in 2007, Jolie maintained she and Pitt remained friends for a long time, and only embarked on romance after his divorce from Aniston.
Moving on: Both actresses were married to Brad Pitt as Aniston was from 2000 to 2005, they are pictured together in February 2001 datingsite voor hoger opgeleiden
Former flames: Brad was married to Angelina from 2014 to 2016, as they are pictured together in November back in 2015
However, she did confess they had started to develop feelings for each other while shooting the thriller.
'Because of the film we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened,' she said.
'I think a few months in I realized, God, I can't wait to get to work.'
Rapport: Gerard could be seen with shaky legs but other guest 50 Cent seemed pleased by his answer as he smiled big and said: 'No no no this is good!'
Fun times: Gerard seemed loose during the appearance
The following year, Aniston addressed these comments in her own cover interview - and branded them 'inappropriate'.
Gerard's actual lovelife was also at the center of some of the questioning on the after show of the program as he was asked about his fling with Real Housewives Of Beverly Hills star Brandi Glanville.
Cohen brought up how 45-year-old wann mit internetbekanntschaft treffen Glanville had came on the program previously and said that she and Butler had a relationship.
Chatting it up: Gerard's actual lovelife was also at the center of some of the questioning on the after show of the program as he was asked about his fling with Real Housewives Of Beverly Hills star Brandi Glanville
Wow factor: Cohen brought up how 45-year-old Glanville (pictured in LA back in October) had came on the program previously and said that she and Butler had a relationship
Eyebrow raising: The 300 star said that when he had met her he had no idea that she was on television or had any fame at all
Yum: The trio took a shot together
The 300 star said that when he had met her he had no idea that she was on television or had any fame at all.
He explained: 'It was kind of a crazy time in my life. Anyway we hung out and had fun and I never saw her again.'
Gerard said later people from TMZ had approached him and asked about his relationship with the reality star to which he replied: 'Whose Brandi Glanville!?'
Casual cool: Butler rocked a denim jacket over a grey shirt, blue trousers and beat up grey suede boots
Dapper: 50 Cent looked handsome in a checked blue suit with patterned Gucci shoes
The actor then continued with a laugh: 'Because I didn't even know her last name. So I'm like "Whose Brandi Glanville?" She got pretty upset about that.'
Gerard and 42-year-old rapper 50 Cent star together in crime/action flick Den Of Thieves.
The dynamic duo also both attended the premiere of the Christian Gudegast written and directed flick in Los Angeles on Thursday night. Den Of Thieves is set for release on Friday in the US with a UK release following on 2 February.
Busy: Gerard and 50 Cent joined co-stars O'Shea Jackson Jr (left) and Pablo Schreiber (second to right at the Den Of Thieves premiere in Los Angeles on Thursday night