Winnaretta Singer inherited her father's massive sewing machine fortune, but she still had to marry an aristocrat to be part of high society. One big problem - she was a lesbian! Fortunately she found the perfect match in Prince Edmond de Polignac. They both loved music, art, and best of all - he was gay too! Together they threw stacks of money at artists and composers whose names we still know today.See omnystudio.com/listener for privacy information.

Al Capone took his wife and son to Miami to try and retire, but he ended up continuing his murderous, bootlegging, tax-dodging ways. When he was caught and sent to Alcatraz, Mae had to work against the system to get him medical care for the syphilis that was destroying his brain. When he finally got out, he went from #1 Public Enemy to #1 Dad!See omnystudio.com/listener for privacy information.

Before Italian-American mobster Al Capone became Public Enemy #1, he fell in love with an Irish girl named Mae, and defied cultural customs by marrying her. They had a son named Sonny, and Al wanted to provide for his family as a legitimate businessman. But (spoiler alert) he fell into a life of crime. And an undiagnosed case of syphilis wreaked havoc on his brain and made him even more ruthless as the years went by!See omnystudio.com/listener for privacy information.

Isaac M. Singer was a struggling actor with an estranged wife, a girlfriend, and 10 kids between the two of them. But his knack for invention helped him launch America's first multi-national business, the Singer Sewing Machine Company. But he couldn't keep his stitches in his britches and eventually he fathered 26 children from 4 different women. His lifestyle needled his business partner & nearly unraveled the entire company!See omnystudio.com/listener for privacy information.

It's high time we checked in on our fellow humans' romances, so once again we turned to the most Ridiculous forum on the web: Reddit. People boldly ask if they are the a-holes in their relationships, but the answers aren't as easy as we thought! Plus Bridezilla vs Bridesmaid Kong, a husband gaslighting with real gas, and some poor people who are dating true f***ing idiots. All this and more here in our latest Reddit Roundup!See omnystudio.com/listener for privacy information.

Bernard Bouriscot worked in the French Embassy in China in the 1960s, where he befriended a man named Shi Pei Pu. Soon, Shi revealed his biggest secret - he was actually a woman in disguise! They fell in love, and Bernard started spying for the Chinese government in order to stay close to her. But Shi had more secrets, and Bernard was in for some shocking truths!See omnystudio.com/listener for privacy information.

After the death of Tsarina Anastasia at the hands of the boyars, Ivan IV was furious. With his 2nd wife, he started the Oprichnina, and one of Russia's darkest periods in history, resulting in the deaths of nobles, peasants, and even his own family. But it wouldn't be until his 8th marriage that his brutal rule came to an end. Don't worry, we somehow still found a few laughs in there!See omnystudio.com/listener for privacy information.

Ivan IV had a grudge against Moscow's nobles ever since they poisoned his mother. So when he was crowned Russia's 1st all-powerful Tsar, he started cutting off their power (by cutting off their heads). His 1st wife Anastasia helped him keep his cool, but when the nobles poisoned her too, Ivan really started to get Terrible.See omnystudio.com/listener for privacy information.

Queen Elizabeth and Robert Dudley were still super into each other after Amy Robsart died, but marrying would be too scandalous. But despite taking on her own suitors, Elizabeth was still incredibly jealous when Robert Dudley hooked up with other ladies! But did Elizabeth and Robert ever actually - you know - DO it?? We dive into all the craziest theories, from trauma and stepdads to incest and Shakespeare. It's never a dull day in Queen Liz's court!See omnystudio.com/listener for privacy information.

Lord Robert Dudley was besties with his childhood friend, Elizabeth Tudor. After she snagged a promotion to Queen of England, she kept him close and eventually fell in love with him. But when Robert's wife Amy mysteriously died, the rumors started flying about what the Queen and her alleged lover might be capable of! Was it an assassination? An accident? Or something... spookier?? Well we think we cracked this 600 year old case!See omnystudio.com/listener for privacy information.