That Justin Timberlake is one fine fellow. While he started out as the ramen-noodle-haired member of the boy band NSYNC, he has clearly developed a stronger fashion sense over the years. The group shot to stardom and everyone not only fell in love with the band, but Justin himself. Since the band disbanded, he launched a solo music career in the new millennium that was even more popular than his hits with NSYNC. Soon came movie deals and awards show appearances and even humanitarian work. And of course, there were loads of romantic dealings sprinkled in!
Justin had quite a love life from the time he was able to date, to his marriage to the gorgeous Jessica Biel. In between those years there were speculations of backstage hook-ups, bedding co-stars and other artists, and too many break-ups to count (but that won't stop us from trying). So here is our list of The 20 Hottest Women Justin Timberlake Has Been with. This guy is super-attractive, as well as talented and just an all-around sweetheart. So you can bet that he had a lot of girls yearning for his attention and it is easy to see why. Here are just twenty of them.
From models and dancers to other music artists and female band members, these girls are all beautiful, but only one of them got the guy in the end! Way to go, Jessica!
20 Elisha Cuthbert
Elisha Cuthbert is an actress and model, so you know she is one fine-looking lady. The Canadian was the main squeeze of one of Just Timberlake’s best friends, Trace Ayala. Rumor has it that Elisha and Justin had a period of intimacy as well. Anyway, the model is clearly referenced in Justin’s hit song “What Goes Around Comes Around.” In the video, Justin and Scarlett Johansson play a couple with a dramatic relationship. They are representing the tumultuous intimacy of Trace and Elisha. The model ended up cheating on Trace. Shame on her! As for Trace, he is now in a secure relationship with Joanna Garcia so don't feel so bad for him.
19 Olivia Wilde
In the Spring of 2011, actress Olivia Wilde seemed to be all over Justin Timberlake’s radar. The two were seen hanging out and partying in Los Angeles like they were wild and free. Justin had recently split from Jessica Biel (but don’t worry, they ended up getting married!) and Olivia was recently divorced (she was previously married to Tao Ruspoli.) Justin and Olivia were co-stars at the time in the film Now, and the relationship sparked headlines among gossip magazines. The romance lasted for a hot second, but the two celebs have managed to do quite well for themselves since then.
18 Olivia Munn
Back in the fall of 2010, Justin was reportedly spending a lot of time with Olivia Munn, even though he was in a serious boyfriend-girlfriend relationship with Jessica Biel. So, how did Justin and Olivia meet up? It turns out that Olivia interviewed Justin to get some more details on the movie he was filming, The Social Network. After the interview, she apparently wasn’t done, because Olivia was driven to a hotel by a private driver with Justin in tow! It can be easy to see how speculations of Justin’s fidelity were flying rampant at this time. Luckily, things cooled off, Justin married Jessica, and all is well.
17 Lindsay Lohan
LiLo is a hot mess, so can we really believe what she says? According to the washed-out celeb, she had sex with Justin Timberlake and a whole laundry list of other guys, including Adam Levine and Zac Efron. Lindsay said that this sexual activity streak was part of her rehab work at the Betty Ford facility. It was about taking a “sexual inventory.” Uh huh. Lindsay entered Betty Ford for drug and alcohol abuse and supposedly had to exorcise her demons, and part of that was sleeping around, we guess. One thing is for sure: we are so glad that Justin didn’t end up with Lindsay in the long run!
Wait, so RiRi and Justin Timberlake were an item? When? This was back in 2009, when there were rumors surrounding the two celebs. After being seen together on a few occasions, people started suspecting that the two were hooking up (while JT was dating Jessica Biel, might we add!) Those suspicions were probably ignited further by the music video collaboration between Justin and Rihanna (they sang “Rehab” together.) The two singers were also spending lots of quality time together at the amfAR Gala, which Justin went to without Jessica. So while it was a brief love triangle speculation, but we know who got Justin in the end!
15 Scarlett Johansson
Scarlett Johansson was featured in Justin’s music video “What Goes Around Comes Around” and portrayed Justin’s love interest. In the video, the two are seen being intimate, fighting, and just being totally cool. Justin and Scarlett were actually acting as Trace Ayala and Elisha Cuthbert (who had a relationship that ended in Elisha cheating on Trace.) Hence, in the video, Scarlett cheats on Justin. Yet, rumor has it that Justin and Scarlett ended up hooking up while on the set of “What Goes Around Comes Around.” Too bad in the music video, Scarlett’s character dies in a wicked crash collision!
14 Cameron Diaz
We still think that Justin and Cameron Diaz would have made an excellent couple, but alas. Besides, Cameron is much too independent. Anyway, they were said to have dated for a hot second, and their breakup came just when Justin was shooting the music video for “What Goes Around Comes Around.” which as I had mentioned, features Scarlett Johansson. There is no telling how his relationship would have been with Diaz if she had been the star of the video! Was Scarlett a rebound girl for JT? Oh well, it looks as though both Justin and Cameron are on good terms now and they have both moved on and had success in their respective fields.
13 Tatyana Ali
2003 sure was a busy year for Justin Timberlake. He was young, he was hot, and he was breaking out into a stellar solo career. So from April to July of that year, he was hanging around with Tatyana Ali. Many people don’t know this name, but the connection between JT and Tatyana goes way back. The two actually met on the show, The Mickey Mouse Club (this is also where Britney Spears and Christina Aguilera got their starts.) That means that Tatyana is also musically gifted. In fact, she sang as an opening act for NSYNC back in the day! She was also the character Ashley on The Fresh Prince of Bel-Air
12 Emma Bunton
Baby Spice and NSYNC’s Justin Timberlake. It’s almost as if the stars aligned on this one. Alas, it must have been too good to be true, because Emma Bunton and JT’s romance didn’t last. In the Spring of 2003, Justin said that he and Emma had gotten it on under the sheets and that Emma was “really gorgeous.” Well, no duh! They got together in London (of course) and were spotted kissing in public a few times. Still, Emma wouldn’t open up about the details and said that she and Justin were “just good friends.” Who doesn’t want some spice in their life?!
11 Staci Flood
Another brief relationship for Justin Timberlake was his romance with Staci Flood. The couple were an item for a couple of months in early 2003. So, who is this girl? Let us jog your memory. Remember the song “Rock Your Body”? Well, the girl in the video was Staci Flood herself! We loved that music video and the sexier Justin Timberlake that went with it. Looking back, now we can see why he dated Staci for a minute. She was smoking hot in that video, too! Staci went on to appear in other music videos, as well as magazines such as Maxim and Lowrider. She released her own album, FLOOD, a few years back.
10 Alyssa Milano
Alyssa Milano is now ruling the celebrity sphere with her powers as a breast-feeding wonder woman, but back in the day, she was dating Justin Timberlake. Still, even in her younger days, she was still super admirable! She was the brief love interest of JT right after he famously split from Britney Spears. Even so, looking back, Alyssa admits that she thought Justin and Brit were a wonderful match for each other. It was pretty devastating when they broke up. You took the words right out of our mouth, Alyssa! That’s okay. Both Justin and Alyssa seem to be doing just fine now.
9 Jenna Dewan
Who is Jenna Dewan? The girl who may (or may not) have been part of the distressing breakup of 2002. Yes, the time when Justin Timberlake and Britney Spears called it quits as boyfriend and girlfriend. Jenna was suspected of being the “other woman,” making the whole thing a complete mess. Jenna was working as a backup dancer and that she ended up being the rebound girl for Justin after he split from Brit. Oh well. As of now, Justin is happily married to Jessica Biel and Jenna is equally as content being the wife of Channing Tatum. Sheesh, some girls have all the luck!
8 Alicia Keys
Back in Justin’s NSYNC days, he was spotted hanging out quite a bit with songstress Alicia Keys. This led many to believe that the two had hooked up and were dating. In early 2002, the two musical prodigies spent a lot of time together, having long meals at each other’s homes, and hugging and kissing. Things seemed to be good, but the canoodling did not last very long. About a month into the speculations, Justin and Alicia went their separate ways and stopped spending so much time together. Perhaps they were never a legit couple at all, but we really can’t blame Alicia for wanting some sugar from Justin!
7 Nicole Appleton
It was a long time ago, but JT and Nicole Appleton hooked up back in 2000. Justin was just 19 years old and was flying high off of the success of the 5-member boy band, NSYNC. For her part, Nicole was another musically-gifted young person. Besides singing, she writes songs and now she works as an actress and as an occasional television presenter. She and Justin were spotted while gallivanting in London, England. This was around the time that Nicole was in the spotlight for her contributions to the band All Saints. Unfortunately, her split from JT was just the beginning of a long line of break-ups for the talented star.
6 Britney Spears
Brit and Justin; yes, it was the relationship of the early 2000s. Remember when they showed up together at an awards show wearing matching denim outfits? Anyway, while both of them have since moved on, they were a hot commodity for a bit. It turns out that lots of people suspects that Britney cheated on Justin, and that the song “What Goes Around Comes Around” is about that relationship drama. No word on how much validity there is to that, but we do know that after Justin and Brit broke up, the song was recorded. And we all know how Brit spent the following few years.
5 Veronica Finn
One of Justin’s little-known ex-girlfriends was Veronica Finn. She was part of an all-girl band called Innosense (we know, lame) in the mid-1990s. According to Finn herself, she and Justin had a great relationship, and the Nsync member was an “absolute sweetheart.” Even so, their romance was a bit difficult because they had to be apart a lot. Both of them were touring with their respective bands and that meant that doing the typical teenage-dating things was super-tricky. And while Justin catapulted to fame and launched his solo career, Finn left music and is now working in the real estate industry.
Both Justin and Fergie are married to other people now, but a few years ago, they were a power couple in the music industry, even if most people don’t remember. In fact, we doubt that anyone could really recall this romance. It was back around 1996 when Justin was just 16 years old and Fergie was a more mature young woman (she was 23.) Fergie was going by the name Stacy Ferguson and she was in the girl-group Wild Orchard. Justin was getting ready to shoot to fame in the boy band, Nsync. It looks like Fergie and JT fell out of sync (hah) and their relationship ended.
3 Danielle Ditto
When he was just 14 years old, Justin dated Danielle Ditto (although at that age, can you even call it “dating”?) Anyway, she was his boo from 1994 to 1996 and guess what? Both of them lost their virginity to each other (aw.) So, since she was the first woman that JT had sex with, she is pretty darn special. You can actually find really adorable photos of and young Danielle and Justin on the Internet. Pictures from their high school dances and teenage escapades portray just how happy this young couple was. So, what happened between those two? We may never know!
2 Mila Kunis
Justin Timberlake and Mila Kunis have not been shy about discussing their romantic dealings. While the two stars were filming Friends with Benefits, they had to portray friends who happen to engage in casual sex together. So, needless to say, Justin and Mila had to spend some time in bed while shooting the film. In a funny moment, Mila actually fell asleep on the set. Justin was supposed to be caressing her in bed, but Mila was dead-tired and actually dozed off. Kind of cute. The film was also a defining moment in pop culture (and mainstream culture,) in which friends-with-benefits started to become socially acceptable.
1 Jessica Biel
Ah yes, the final lady here is the one that Justin actually ended up marrying (and having a baby boy with!) Jessica and Justin were first spotted as boyfriend and girlfriend back in 2008. They weren’t without their ups and downs, and actually split up in 2011, but they soon rekindled their romance. Jessica, who shot to fame in the family drama 7th Heaven, attended her co-star’s wedding and had Justin in the wedding with her! In 2012, it was Jessica’s turn to be a fiancée. In October 19, 2012, they got married in Italy and will hopefully have a wonderful, and smooth future ahead of them.