- In June 2000 he was the richest man in Italy ($ 12.8 billion, according to "Forbes") and the leader of the biggest conservative political party in Italy, "Forza Italia", founded by him on January 18th, 1994. He is probably the most controversial political figure in Italy. His entry into politics was immediately the subject of a large national debate (which still goes on), which has divided the Italian people essentially in two parts. Italians moderates considered him the savior of his country from the danger of communist coalition (at that time led by Achille Occhetto), and because of that became the subject of a judicial persecution by the left politicized judiciary which is unprecedented in the history of Italy. The other part considered him the worst Italian criminal ever existed, accused in more than 20 court proceedings and who entered politics only to save himself from jail and expand his private business interests to the detriment of the rest of the nation. He has always fought with a particular force the left coalition in Parliament. It is also famous a hard verbal confrontation that took place in the European Parliament on July 2nd, 2003, with the German eurodeputy Martin Schulz: he heavily criticized Berlusconi and his government and so Berlusconi told him: "Signor Schulz, so che in Italia c'è un produttore che sta montando un film sui campi di concentramento nazisti: la suggerirò per il ruolo di Kapo. Lei è perfetto!".
- He was nicknamed "Il Cavaliere" ("The Knight") because on June 2nd, 1977 he became the youngest member of the Ordine Cavalleresco al Merito del Lavoro, an Italian order of knighthood reserved to entrepreneurs. He has given up this honor in 2014.
- In 1994, when he entered politics, resigned all the offices he held in his companies, except the office of chairman of A.C. Milan S.p.A. (1st division soccer team). The 2 children he had with his first wife, Carla Elvira Lucia Dall'Oglio (born on September 12th, 1940), are now among with the top directors of his group: Marina Berlusconi is vice-chairman of Fininvest S.p.A. (general holding company of Berlusconi's group) and Pier Silvio Berlusconi is vice-chairman of the Mediaset Group and chairman and chief executive of R.T.I.
- He met and fell in love with actress Veronica Lario in 1980 when he was still married to first wife, Carla. They married on December 15th, 1990, and had 3 children: Barbara Berlusconi, Eleonora (born on May 7th, 1986) and Luigi (born on September 27th, 1988).
- Took charge of Milan in 1986, transforming the club into one of the best in Europe and cheering them to four European Cup titles and seven Italian titles.
- Quits A.C. Milan presidency to comply with the law that prohibits the country's premier from running private enterprises. (December 2004)
- Has his look-alike puppet in the French show Les Guignols de l'info (1988).
- Prime Minister of Italy for 3 times: from May 10th, 1994, to January 17th, 1995, from June 11th, 2001, to May 17th, 2006, and from May 8th, 2008, to November 16th, 2011.
- Is portrayed by Nanni Moretti, Elio De Capitani and Michele Placido on The Caiman (2006), a movie about his vicissitudes, which was released just days before the 2006 general elections and became a blockbuster in Italy.
- Berlusconi lost the political elections 2 times: on April 21th, 1996, and on April 9th and 10th, 2006, this time for just about 24,000 votes out of 38 million. On February 24th and 25th, 2013, for the first time in the history of Italy no coalition has obtained an absolute majority in the Senate of the Republic, causing 2 months of political stalemate.
- Underwent emergency heart surgery in June 2016.
- He is the firstborn of Rosa Bossi and Luigi Berlusconi (March 27th, 1908 - 1985). He had a sister, Maria Francesca Antonietta (June 9th, 1943 - February 25th, 2009) and has a brother, Paolo Berlusconi (born on December 6th, 1949).
- Grandfather of Eleonora's children: Riccardo and Flora Binns; Barbara's children: Alessandro and Edoardo Valaguzza, Leone and Francesco Amos Guerrieri; Piersilvio's children: Lorenzo Mattia, Sofia Valentina, and Lucrezia Vittoria; Marina's children: Gabriele and Silvio Vanadia. Former brother-in-law of Mariella Bocciardo and Antonia Rosa Costanzo. Uncle of Alessia, Luna Roberta, Davide Luigi and Nicole Rose (Paolo's children).
- In January 2013 he was criticized for defending Benito Mussolini's alliance with Adolf Hitler during World War II. Berlusconi said Mussolini wanted to be on the winning side, which in June 1940 looked likely to be Germany.
- His father, Luigi Berlusconi (1908-1989), was a bank employee, and his mother, Rosa Bossi (1911-2008), a housewife.
- In April 2017, Berlusconi appeared in a video promoting a vegetarian Easter campaign. He was shown cuddling lambs he had adopted to save from slaughtering for the traditional Easter Sunday feast; he did not confirm or deny whether he himself is a vegetarian.
- Berlusconi had made disparaging remarks about Finnish cuisine during negotiations to decide on the location of the European Food Safety Authority in 2001. He caused further offence in 2005, when he claimed that during the negotiations he had had to "dust off his playboy charms" to persuade the Finnish president, Tarja Halonen, to concede that the EFSA should be based in Parma instead of Finland, and compared Finnish smoked reindeer unfavourably to culatello. The Italian ambassador in Helsinki was summoned by the Finnish foreign minister.
- Berlusconi first entered the media world in 1973, by setting up a small cable television company, TeleMilano, to service units built on his Segrate properties.
- In the night of 15-16 December 2009, a 26-year-old man was stopped by police and Berlusconi's bodyguards while trying to gain access to Berlusconi's hospital room. A search revealed that he carried no weapons, although three hockey sticks and two knives were later found in his car. The suspect was known to have a history of mental illness and mandatory treatment in mental institutions.
- During his university studies, he was an upright bass player in a group formed with the now Mediaset Chairman and amateur pianist Fedele Confalonieri and occasionally performed as a cruise ship crooner.
- On 6 November 2008, two days after Barack Obama was elected the first black US president, Berlusconi referred to Obama as "young, handsome and even tanned". On 26 March 2009 he said "I'm paler [than Mr. Obama], because it's been so long since I went sunbathing. He's more handsome, younger and taller.".
- After completing his secondary school education at a Salesian college, Berlusconi studied law at the University of Milan, graduating with honours in 1961, with a thesis on the legal aspects of advertising.
- Two days after the 2009 L'Aquila earthquake, Berlusconi suggested that people left homeless should view their experience as a camping weekend.
- He wrote A.C. Milan's anthem with the Italian music producer and pop singer Tony Renis and Forza Italia's anthem with the opera director Renato Serio.
- In 2020, Wondery released a podcast about Berlusconi's rise and fall entitled Bunga Bunga hosted by comedienne Whitney Cummings.
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