Professional baseball players are a rare breed. With superhuman hand-eye coordination, big paychecks, and athletic builds, they have it easier than the average male when it comes to attracting the opposite sex. Sure, not everything goes well in the romantic fields of war (as you’ll see below), but no other sport has elicited as many athlete-celebrity relationships as Major League Baseball.

Perhaps the most famous one of all-time involved Yankees great Joe DiMaggio, whose greatest achievement on the diamond — a 56-game hitting streak — ended 74 years ago today. So, in honor of The Yankee Clipper, here are some of the most memorable baseball player/celebrity relationships, starting with the one that started them all:

Joe DiMaggio

His Significant Other: Marilyn Monroe

Legendary slugger Joe DiMaggio and blonde bombshell Marilyn Monroe famously met back in 1952 and supposedly spent the first night together. The pair eloped in January of 1954, but the relationship was rocky at best. DiMaggio’s son recalled one incident in which things got physical between the famous couple.

“I was asleep downstairs and I woke up to the sound of my father and Marilyn screaming . . . After a few minutes, I heard Marilyn race down the stairs and out the front door, and my father running after her. He caught up to her and grabbed her by the hair and sort of half-dragged her back to the house. She was trying to fight him off but couldn’t.”

Before year’s end, Marilyn filed for divorce from Joe. Even as Marilyn had affairs within the Kennedy family, and as she spiraled out of control with substance abuse, they continued to see each other. Sadly, in 1962, Marilyn was found dead from a supposed drug overdose. DiMaggio would continue to send flowers to her grave until he passed away in 1999.

Chuck Finley

His Significant Other: Tawny Kitaen

You can file this relationship under “dysfunctional.” Tawny and Chuck married in 1997, but it wasn’t until 2002 that the sporting world got insight into how their coupling had crumbled. On April 1 of that year, Kitaen was arrested for physically abusing her husband. On April 4, Chuck filed for divorce along with a restraining order. Finley alleged that his wife was an aggressive drug abuser: A pharmacist testified that she was under the spell of a litany of anti-depressants.

Legal troubles continued to follow Kitaen; in 2006, she was arrested for possession of cocaine; in 2009, she was arrested for DUI. Hopefully the actress who famously starred in several Whitesnake videos has gotten her life together by now.

Alex Rodriguez

His Significant Others: Madonna/Cameron Diaz/Kate Hudson/Torrie Wilson

When you’re talented, good-looking, and one of the highest-paid players in baseball, I imagine that having luck with the ladies is not something you fret over. Case in point: Alex Rodriguez. A-Rod has been linked to tons of women over the years, seeing the likes of Madonna, Kate Hudson, among others.

After five years of marriage to his gorgeous wife Cynthia, A-Rod supposedly cavorted around town with Madonna, helping to essentially disintegrate his marriage. For the past three years, A-Rod was dating the stunning former WWE personality Torrie Wilson, but the relationship apparently ended towards the end of 2014.

David Justice

His Significant Other: Halle Berry

David Justice and Halle Berry were sitting atop the world at one point. He was the ultra-talented player who appeared in six World Series, and she was one of the most beautiful and well-paid women in Hollywood. The pair wed in 1992, but they split up just four years later, with Berry seeking a restraining order from Justice. In a 1996 interview with People, Berry spoke on the heartbreak she endured after the divorce.

“This is a painful, painful chapter in my life. For four years David was part of my life, every day, every hour. I do keep telling myself that this is one of life’s lessons, and as long as I can learn something from it, then all the pain will be worth it.”

Derek Jeter

His Significant Others: Jessica Biel/Mariah Carey/Lara Dutta/Minka Kelly/Jessica Alba/Hannah Davis

Like A-Rod, former Yankee superstar Derek Jeter has been linked to many women, all of them gorgeous and famous. Currently dating swimsuit cover model Hannah Davis, Jeter has also been seen out with the likes of Jessica Biel, Jessica Alba, Minka Kelly, and many more. It’s been rumored that Jeter and Davis are close to being engaged, so maybe she’ll finally take him off the market.

Barry Zito

His Significant Others: Alyssa Milano/Paris Hilton/Amber Seyer

A first round draft pick in 1999 and Cy Young winner in 2002, Barry Zito was one of the hottest pitchers at the turn of the century. He was also doing well for himself away from the mound, dating Alyssa Milano in 2004, as well as Paris Hilton. Zito is currently out of the bachelor’s life: He wed his current love, and Miss Missouri, Amber Seyer in 2011.

Josh Beckett

His Significant Other: Leeann Tweeden

Josh Beckett was one of the best pitchers in the league for almost a decade before injuries caused him to retire last year at the age of 34. The right-hander used to be seen around town with TV personality and model Leeann Tweeden, but a fateful interview with FHM changed all that. Speaking on the topic of sex, Tweeden allegedly said, “My boyfriend knows how to hit the strike zone. He’s got a good change-up. We could go all day with this… he knows how to work the mound or the mounds.”

Pretty salacious stuff. Beckett apparently did not like the interview, and the couple broke up soon after. Tweeden didn’t get the memo that you’re not supposed to give away a pitcher’s secrets.

Matt Kemp

His Significant Other: Rihanna

Ms. “B*tch Better Have My Money” and Matt Kemp looked like a tight item at one point in history. After Ri Ri and Chris Brown broke up following an ugly incident in 2009, Kemp and Rihanna could be spotted at NBA and MLB games. The couple split in 2010, and Kemp cited that their travel schedules were to blame.

“It was pretty much overwhelming,” Kemp said. “It’s not something I’m used to. I’m not used to going to a grocery store or to just somewhere simple and people following me around. It’s overwhelming.”

The pair seemingly dated again in 2013 after being seen having dinner together in L.A., but they have since gone their separate ways.

Justin Verlander  

His Significant Other: Kate Upton

Competing for a spot in the cutest couple in all of sports, Verlander and Upton have been an item for a little while now. Things got spicy, though, when a massive photo hack scandal unleashed a plethora of naked photos of the pair.

“I grinded through it… Kate’s there a lot for me,” he said following the leak. “And we’re just normal people. You know, normal relationship, believe it or not.”

There’s nothing really normal about two really good-looking and famous people dating. That doesn’t happen in real life… just baseball.