1990
Sheen allegedly shoots then-fiancée Kelly Preston in the arm. The real story: She picked up a pair of Sheen’s pants, the pocket of which contained a loaded gun, which accidentally discharged. She left Sheen shortly after. Gosh, we hope she ended up marrying a far more stable, less controversial actor! 
1990
Sheen and Estevez reunite to make Men at Work, a meh comedy about two garbage men that just so happens to feature the greatest sh*t gag in the history of cinema.
1991
Sheen stars in Hot Shots!, a comedy spoof that earns more than $180 million worldwide. The film, which steals blends elements of Top Gun and Airplane, also featurs legendary actor Lloyd Bridges and that guy from Princess Bride and Saw. Not surprisingly, the 1993 sequel, Hot Shots! Part Duex, is terrible.
1992
For the paltry sum of $93,000, Sheen purchases the infamous “Buckner Ball” — the same baseball that squeaked between Bill Buckner’s legs, costing the Boston Red Sox the 1986 World Series. Sheen later sells the ball for $64,000, proving he learned absolutely nothing on the set of Wall Street.
1995
Sheen cops to being a client of pricey “Hollywood Madam” Heidi Fleiss, admitting to spending close to $50,000 for her services. Sheen’s then-wife Donna Peele gets all agro about it and leaves him after just 14 months of marriage.
1997
Sheen stars in Money Talks with Chris Tucker, which earns lackluster reviews. In the same year, he’s given two years’ probation, a $2,800 fine, and a year’s suspended sentence after pleading no contest to battery charges for smacking around his former model-actress girlfriend, Brittany Ashland.
