When Saint Augustine was a younger man, traveling in Carthage, he engaged in what some might call "debauchery". Gambling. Women. Coveting his neighbor's ox. You name it. During this time he famously prayed to God: "Grant me chastity and continence, but not yet." He was torn between living the perfect, Godly life, and the pleasures of the flesh. He thought, quite astutely, that it would be nice to have a few more years in debauchery, and then find salvation later in life. It's an absurd prayer to give at the time, but it's also basically what he did. He slowly absolved himself of his Earthly desires, and dedicated himself over time to religious ideals as he got older.
David Hume apparently also gambled frequently. Hume was a bit into debauchery as well, when he traveled to Paris, and he liked gambling precisely because of how it mirrored his ideas on causality. In gambling, past actions have no impact on future results, and yet people tend to see patterns like "being on a hot streak". Hume could see that these were purely psychological patterns, and wondered how inductive reasoning works at all.
Descartes was a gambler too I guess. Well, actually the only source I found for this was a gambling site, which listed him as a famous gambler, who apparently also had a wild streak in his youth. And, well, it's not as though I don't trust the good folks at onlinepokerrealmoney.co.uk to give the most trustworthy historical research, but I guess take it how you will.

My God. That was terrible.

some people think this comic is educational lol

Nietzsche, later on, writing aphorisms: "Let's see, how you can express that you hate women in a way that sounds deep..."

Happiness is a spook.

In the spring of 1845, Max Stirner gambled away all of his wife's inheritance on a centralized milk distribution business. Supposedly he wanted to use the business to both prove his ideas would work in practice, and to set him up for life, so he wouldn't have to worry about money and could just write. Well, the business failed almost immediately, because he had trouble finding customers, possibly because of his inability to relate to his customers, his inexperience in business, and him alienating people with his strange egoistic anarchist politics (details are scarce, so it is mostly speculation). He was made fun of ruthlessly by his contemporary intellectuals, and his wife of two years left after he blew all of their money. For the rest of his life he lived off the very meager income he got from writing.
To add insult to injury, the idea of a centralized milk distributor was a quite good one, and a highly successful business in the same vein popped up soon after, according to his biography by John Henry Mackay:

How sound the idea of the enterprise was, in spite of the unsuccessful attempt, was later shown by Klingel-Bolle, which is well known today by every Berlin child. It mixed its milk, if not with water, then with a big portion of Christianity and thus contributed not inconsiderably to the success of its business.

It turned out that Christianity worked better than anarchism as a selling point for milk. Who could have predicted that? Not Max Stirner, apparently.

It turns out that when you agree to play a game with Camus, you implicitly agree to the "Camus Contract". That means Camus is gonna do whatever the fuck he wants.