Silvio Berlusconi will learn tonight whether he has a future in politics when the Italian Senate vote on his expulsion from parliament.
Ahead of the vote, we look at the former prime minister's most famous gaffes and controversies.
1. Describing Obama as 'suntanned'
Silvio Berlusconi caused controversy in 2008 when he described President Obama as "handsome, young and also suntanned".
Failing to learn his lesson, Mr Berlusconi repeated the joke a year later saying: "Ah, Barack Obama. You won't believe it, but the two of them sunbathe together, because the wife is also tanned."
He described critics who took offence to the comments as "imbeciles without a sense of humour".
2. Trying to make light of the sex scandals
Mr Berlusconi's diplomatic errors have been accompanied by a string of scandals about his private life.
The former prime minister consistently tried to dismiss the scandals.
In April 2011 he said: "When asked if they would like to have sex with me, 30% of women said, 'Yes', while the other 70% replied, 'What, again?'"
3. Bunga bunga parties
Mr Berlusconi was sentenced to seven years in prison in June after being found guilty of paying for sex with an underage prostitute and abusing his power while in office.
It emerged that the former prime minister had called a police station to request the release of the girl - who had attended his so-called "bunga bunga parties" - after she was arrested for theft.
The former prime minister is currently appealing against his conviction.
4. Offending Italy's gay community
After being engulfed in the "bunga bunga" scandal, Mr Berlusconi sought to defend his actions.
However, the politician caused fury telling an audience: "It is better to have a passion for beautiful women than to be gay."
5. Being rude about a female political rival's looks
When prime minister, he provoked outrage when he suggested political rival, Mercedes Bresso, was "always in a bad mood" because when she gets up in the morning and "she looks at herself in the mirror to put her makeup on - and sees herself, her day is already ruined.”
Ms Bresso hit back at Berlusconi saying she is "better preserved than him, even without plastic surgery".
6. 'Dusting off my playboy charms'
In 2005, Mr Berlusconi offended Finland when he boasted that he had to "dust off my playboy charms" to convince Finland's female president, Tarja Halonen, to hold a European Food summit in Italy before criticising Finnish cuisine.
7. Telling earthquake survivors to enjoy a 'camping weekend'
Following the devastating L'Aquila earthquake in 2009, which claimed the lives of 309 people and left over 17,000 people homeless, Mr Berlusconi said that those made homeless should see the experience as a "camping weekend".
8. Offending China
In 2006, he declared: “I am accused of having said that the [Chinese] Communists used to eat children.
"But read the black book of Communism and you will discover that in the China of Mao, they did not eat children, but had them boiled to fertilise the fields.”
9. Calling a German MEP a 'concentration camp guard'
He responded to criticism from German MEP Martin Schultz over his alleged mafia links by referring to him as a "concentration camp guard".
“I know that in Italy there is a man producing a film on Nazi concentration camps - I shall put you forward for the role of Kapo (a guard chosen from among the prisoners) - you would be perfect.”
10. Noisy G20 photocall
During an official G20 photocall in 2009, the Queen was seemingly 'not amused' by the noise created by the then Italian prime minister.
In footage from Buckingham Palace, Mr Berlusconi is heard to shout, "Mr Obama!" at the US President who is sat just in front of him.
The President replies quietly, "Mr Berlusconi".
The Queen appears to say, "What is it? Why does he have to shout?", prompting laughter from other leaders.