I just discovered this thread, let's get give some contribution...
Gianni de Michelis is probably the most hipster politician in Italian politics. Firstly, it's relatively easy to put him as President of the Council, since he had a brilliant career; he had been Minister of State Partecipations from 1980 to 1983, Minister of Labor from 1983 to 1987, president of the parliamentary group of the PSI from 1987 to 1988, Vice-president of the Council from 1988 to 1989 and Minister of Foreign Affairs from 1989 to 1992. He was the second most important member of the Italian Socialist Party (PSI) after Bettino Craxi and one of the most influential political figures in '80s Italy. But he also was a womanizer, who employed tens of women in his staff only for their beauty. He was a dancing lover, and he wrote and published in 1988
Where do we go to dance tonight?, a guide on the top 250 night clubs in Italy. He also was President of the Italian Basketball League from 1984 to 1992, where he obtained from RAI a 50 billion (lire, not euros, obviously) TV rights deal that gave Italian basketball movement one of his greatest boosts. His best moment would have been in the 80s, I'd say, because he rose in that era, he reached high position and public visibility and in the 90s Tangentopoli will wash away every possibility for him to get even near Palazzo Chigi.
Giovanni Spadolini maybe shouldn't be there, since he actually
has been a President of the Council, but only for a year and a half, before falling for the dissociation from the government majority of the PSI. But Spadolini had more potential than that. Prominent journalist, he entered politics in 1972, and less than a decade after he was not only president of the Council, but the first President of the Council not member of DC (Christian Democracy). Spadolini was in fact member of the Italian Republican Party (PRI), a minor party which generally allied with Christian Democracy. In the election after the fall of his government, the 1983 political elections, PRI took 5,08% of the votes, the highest result for the party since
1900. In Turin, PRI was even the third party, over PSI and behind only DC and PCI. Spadolini became Minister of Defence, and he was there during Sigonella crisis, where Italian and American military forces almost came to blows in the NATO base of Sigonella in Italy over some PLO member. Spadolini here was in total disagreement with President Craxi, who was confrontational towards the US. A pair of years later, Spadolini found himself away from government jobs for enmity with the prominent leaders of DC and PSI that ruled the country that day, namely Craxi, Andreotti and Forlani. Spadolini is extremely interesting because he was in contrast with the politics of his era. When DC and PSI were moving to a third-positionist filosofy in foreign affairs, Spadolini was an ardent Atlanticist and supporters of US and NATO. When Tangentopoli blew away the cover for the mountain of corruption in Italian politics, Spadolini was one of the few top figures that ended up clean. He was an atheist (the first atheist president of council), and deeply believed in the importance of laicity in state and society. He also was one of the most ardent supporters of a separate Ministry for Cultural Heritage, and the preservation of Italian culture, history and archeological patrimony was always of paramount importance for him. I think he should deserve more attention and could have had a greater impact on Italy.
Toni Iwobi is a man born in Nigeria, who married an Italian woman, got citizenship through that and founded a business in IT. Around 90s/2000s he entered in politics, mostly at a local level. But in 2018 his political career took a great upturn, with him being elected to the Italian Senate. What's the matter? Well, the party he's part of in all that - it's
Lega Nord. Yep, the Lega Nord that always had problems with anyone that wasn't Northern Italian. Yep, the Lega Nord that in 2014 said that after all the South is still Italy and that North and South must be united to face the ultimate menace -
immigration. Which means "Arabian-African immigration". To sum it up for Americans, Iwobi is like a Black Dixiecrat. I have no idea about how he can become President of the Council. But if he isn't hipster I don't know who is.
Going outside of Italy,
Edward Makuka Nkoloso once run as Mayor of Lusaka and lost. If he won that, he could have had a base to the Presidency of Zambia. If you ask why it should be interesting, I suggest you to read his Wiki bio. Only hints:
afronauts and
witchcraft medicine.