Derek Jeter vs Justin Timberlake: Top 5 Hottest Girlfriends

Derek Jeter vs. Justin Timberlake

The two greatest American bachelors still on the prowl today.

John Mayer used to give them a run for their money, but women have scorned him since he referenced Jessica Simpson as "sexual napalm."

So, let's settle the debate once and for all.

Who has dated hotter girls? Jeter or Timberlake?

I'll compare their five hottest girlfriends (in my opinion of course) to determine the ultimate winner.

5. Vanessa Minnillo—Jeter

The soon to be Mrs. Nick Lachey dated Jeter until 2006, when he broke things off.

Minnillo, most notable for being Miss Teen USA and the former host of Total Request Live (TRL) on MTV, went on to meet Lachey on the set of his music video "What's Left of Me".

She then came under public fire because she supposedly contributed with breaking apart Lachey and then wife Jessica Simpson.

There had been some speculation that Jeter and Lachey had some issues over Minnillo, but Jeter said that he was happy for them.

The fact of the matter is they both were winners because they dated the smoking hot Minnillo, while Jeter moved on to the next one.

5. Kate Hudson—Timberlake

There have been multiple rumors that Justin Timberlake has dated Kate Hudson at one point or another.

What makes this more meaningful to the list is that we all know that Hudson was key to Alex Rodriguez's success that won both him and Jeter the 2009 World Series.

The fact that A Rod could have been getting Timberlake's "sloppy seconds" is an added bonus for him and Jeter.

4. Jessica Biel—Jeter and Timberlake

So hot that they both got a shot.

Much is being said now about Timberlake breaking it off with Jessica Biel and whether or not that Mila Kunis or Rihanna had anything to do with it.

Regardless, she is gorgeous, but Jeter clearly wins here for getting to her first.

3. Jessica Alba—Jeter

Man, what I would do for a chance.

One of the hottest MILFs alive today, Jeter had his opportunity back in the mid-2000s, but it never worked out.

Now she is married to some guy named Cash, which Jeter has a lot of.

Looks like Jeter is the ultimate winner because he got to Alba first and gets to spend his money instead of being named after it.

3. Britney Spears—Timberlake

Man, remember how groundbreaking this news was at the time?

Timberlake was in N' SYNC at the time, and squashed multiple rumors by going public that he was dating Spears.

This is also before Spears went insane, married Kevin Federline, dangled her baby out a window, shaved her head and did a number of other ridiculous things.

But credit JT for getting Britney at her peak, and possibly being the first to cash in.

2. Adriana Lima—Jeter

Holy...

Jeter dated this Victoria's Secret Angel back in 2006. Interesting to note that she told GQ that sex is for after marriage, so maybe he isn't as lucky as we all think.

Their relationship was short-lived, and Lima is now Mrs. Marko Jaric.

So not only does Jaric make millions of dollars to score 7.1 ppg in his career, but he also married one of the hottest girls on the face of the Earth.

Someone please present Jaric with the "Luckiest Man in the World" award.

2. Cameron Diaz—Timberlake

Maybe Timberlake is the only threat to the Yankee dynasty, as he has dated four smoking hot girls that are either linked to Jeter or A-Rod.

JT dated Diaz from 2003 to 2006, and now she very publicly dates Alex Rodriguez.

Quick side note: I am going to make sure that my son dedicates every waking moment to being either an athlete or a musician.

Looking through the dating resumes of even the most obscure athletes or guitar players makes me question why I graduated with a degree in finance and now work long hours, while these guys get to have fun for a living. Must be nice.

1. Minka Kelly—Jeter

The soon-to-be Mrs. Jeter?

The NY Post reported last year that the two were going to get married, but Jeter said that wasn't true, yet.

So there still remains the possibility that they will get married, but one thing is for sure, we know what will keep Jeter busy after his days with the Yankees are done.

1. Scarlett Johansson—Timberlake

Unbelievable.

Rumors began circulating back in 2007, when Johansson appeared in Timberlake's "What Goes Around..." video.

They have been linked to being on-again, off-again ever since.

Jeter is also linked to having a relationship with her at some point.

What is apparent though, they both got to tout some serious assets on their arm if you know what I mean.

And the Winner Is...

I mean it's not even close: Derek Jeter.

While Justin Timberlake has dated some stunningly gorgeous girls, Jeter's resume is as thick as a phone book, and Jeter dated two of them before Timberlake.

If Jeter does get married to Minka Kelly and Timberlake starts dating Mila Kunis (as many have speculated), that could leave Timberlake at the top of the mountain.

One thing's for damn sure though, they are doing better than the rest of us when it comes to the dating resume department (and the money department...and the fame department).

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