Whatever your politics it's hard to deny John Key's had a fascinating run as New Zealand's commander in chief of "banter".
As New Zealand adjusts to the news of his resignation, we count down the five most cringe-worthy moments from his 8 years of "no filter" leadership.
5. John's vasectomy
Journalists weren't sure what to expect at today's news conference and they certainly didn't see John's unprompted vasectomy disclosure coming in 2010, either.
4. Down to meme
John's done planking, Gangnam Style, and even the mannequin challenge but his go at "derp-face" was debatably the most awkward. Has there ever been a Prime Minister more down with the kids?
Here's his take on Gangnam style, for comparative purposes.
3. THAT handshake
Prime Minister John Key's unusual three-way handshake with All Black captain Richie McCaw and International Rugby Board chairman Bernard Lapasset is set to go down as one of the more hilarious public moments of his tenure.
The Rugby World Cup was a hotbed for leadership slip-ups, with John Key's "troaty" slip of the tongue delighting viewers.
2. 'Gay red top'
John Key used "gay" as a synonym for "weird" on a radio show in 2012, drawing condemnation from the rainbow community, including Sir Ian McKellan. He said he picked up the term from his children and had no intention of seeming homophobic.
1. The ponytail saga
Key made international headlines for pulling a waitress's hair at an Auckland cafe in 2015, explaining he grabbed her hair "in the context of a bit of banter". In an anonymous blog post, the waitress said Key persistently tugged on her "tantalising" ponytail, having approached making "scary, suspense sound effects, like the music from the movie Jaws".
As it turned out, John and ponytails go way back.
Derive McNeill has since thanked the man for working in the mental health sector.