Since debuting on the popular 1980s sitcom Who’s the Boss?, actress Alyssa Milano has captured the hearts of fans around the world. The 5-foot-2 brunette has appeared in some of the most popular television series ever created. Melrose Place, Charmed, and Mistresses are just a few of the shows she's been featured in.
Besides being an accomplished actress, the native of Brooklyn, New York has also worked as a producer, model, and even a singer. When she isn’t working, the stunning actress is rooting for her favorite baseball team, the Los Angeles Dodgers. Milano is not only beautiful, but she is also the girl who enjoys watching (and discussing sports) which makes her all the more appealing to her large male fanbase.
However, Milano not only follows Major League Baseball, she has even dated a few star players of the years. Carl Pavano, Barry Zito, and Brad Penny have all been romantically linked the stunning actress. Apparently, she had a thing for pitchers, as all three players called the pitching mound home over the course of their careers.
While things didn’t work out between Milano and her baseball exes, after seeing these 15 photos, the retired pitchers may wish things had turned out a little differently.
15 Red Hot
This red outfit is red hot. Milano has been the subject of hundreds of gorgeous photographs over the course of her illustrious career. That being said, this pic is easily among her best, which is really saying something given the New Yorker’s body of work. This image shows the actress in peak physical condition, seemingly void of any physical flaws. The red skirt, which can only be described as figure-flattering, helps to showcase Milano’s washboard abs. If the pop culture star looked any hotter, she might literally burst into flames.
Milano Moment: Prior to dating several baseball stars, Alyssa Milano was involved with actor Corey Haim. Haim was a major star (and teen heartthrob) in the 1980s. He is probably best known for staring the cult classic, The Lost Boys.
14 Laid Back
Alyssa Milano is an actress that always seems to come across as a natural in front of the camera; this holds true for modeling as well as acting. In this pic, the former Who’s The Boss? star can be seen posing in a black dress and revealing top. The gorgeous brunette looks cool, calm, and collected as she lays back with her arm stretched over her forehead. This image was taken while Milano had her hair very short, a style the definitely worked for the television star.
Milano Moment: While Milano is best known for being a television actress, she has also stared in several movies over the years. In one of her early roles, she played Jenny Matrix, Arnold Schwarzenegger's character’s daughter, in the 1985 action film, Commando.
13 A Mesmerizing Mermaid
A mermaid is a mythical creature with the upper body of a human and the lower body of a fish. In folklore, mermaids are often associated with events like storms and shipwrecks. As we can see her, Milano makes an excellent mermaid in this photo, as she poses on a rock and stares into the camera. This relatively recent photo shows, that at 44 years of age, Alyssa Milano remains one of the hottest actresses in the business. There are definitely more than a few sailors who would love to run into the stunning brunette on their voyage.
Milano Moment: Milano is arguably best known for playing the role of Samantha Micelli on the popular sitcom, Who’s The Boss? The show’s original run lasted from 1984 until 1992.
12 A Leg Up
Milano delivers yet another amazing photo in her flower print dress. Images such as this one might lead one to conclude that breathtaking celeb has clearly mastered the art of modeling. The 5-foot-2 starlet shows viewers a little bit of leg in this steamy photo. While putting one’s feet (or foot in this case) on the furniture is considered impolite; sometimes bending the rules a little can result in the great photograph, as appear to be the case here. When it comes to looking fantastic, it’s fair to say Alyssa Milano has a leg up on the competition.
Milano Moment: Alyssa Milano was born in Bensonhurst, Brooklyn, New York on December 19, 1972. Her father, Thomas Milano is a film editor. Her mother, Lin Milano work as a talent manager and fashion designer.
11 View From The Back
This Instagram post show the Los Angeles Dodgers superfan in a pair of jeans and a stylish black top. The picture was taken back in 2007 when she was sporting longer hair. Milano is fortunate to be able to look equally amazing with both long and short hair. The popular actress shows off her modeling chops, once again, with a captivating over-the-shoulder stare. When it comes to being a photogenic celebrity, she is clearly in a league of her own.
Milano Moment: Milano began acting at the age of 7, when (without her parent's knowledge) one of her babysitters decided to audition her for one of the main parts in a touring company’s version of the Broadway musical, Annie. Despite competing against roughly 15,000 candidates, Milano ended up landing the role.
10 Swimsuit Fun
The actress shows off a bikini bod that would put most Sports Illustrated swimsuit models to shame, in one of her popular Instagram posts. The throwback photo from 2013 shows Milano taking part in a shoot for the men’s magazine, Maxim. Maxim often features some of the hottest women in both sports and entertainment; as we can see here, Milano definitely fits the bill. If the whole acting thing didn’t work out, the TV star would have likely had a great deal of success modeling swimsuits, such as the one on display in this photo.
Milano Moment: Alyssa Milano made her film debut in the 1984 drama, Old Enough. While it was a low-budget film, Old Enough did manage to win an award at the Sundance Film Festival.
9 Under The Boardwalk
Milano appears to be enjoying a day of modeling at the beach in an outfit which can be described as both stylish and fun. In the pic, the former singer shows off her trademark smile and a set of teeth that any dental professional would be proud of. One could make a strong argument that Milano is as good at modeling as she is at acting. The famous star steals the show with an image that could easily be featured in an Alyssa Milano-themed calendar.
Milano Moment: Milano’s marriage to talent agent David Bugliari in 2009 wasn’t her first. In January of 1999, she married a man by the name of Cinjun Tate. Tate, while not a household name to today's music fans, used to sing for the band Remy Zero, who performed the theme to Smallville. The couple's marriage lasted a little over a year before they divorced in early 2000.
8 The Boa
Milano looks every bit the Hollywood star, with her eye-catching black boa, as she gazes seductively into the camera. The actress’s flirtatious grin helps make this photo one of her very best. The steamy starlet looks ready to be on the cover of a magazine with yet another outstanding photo that her legions of fans around the world are sure to appreciate for years to come. One would hard-pressed to find a better-looking woman than Alyssa Milano in her prime, which one could argue, she is still in.
Milano Moment: Milano was previously engaged to actor Scott Wolf. Fans of '90s television will likely remember Wolf as a cast member of the popular drama, Party of Five. Despite the engagement, the couple never officially wed and broke up roughly a year after the proposal (1994).
7 Shoulder Shot
The stunning star reminds us why she is one of the most popular people in the Hollywood with this amazing photo. Milano can be seen wearing a tight silver dress that reveals some skin on the side. The actress doesn’t appear to be able to produce a bad picture, even if she tried. Not everyone could pull this particular outfit off (figuratively speaking), but as we can see, Alyssa Milano is more than up to the task.
Milano Moment: While Alyssa Milano allegedly dated three different baseball players, she didn’t go out with any of them for very long. Her relationships with former Twins pitcher Carl Pavano and former Red Sox standout Brad Penny each lasted about two months. Her relationship with Barry Zito, which lasted roughly four months, was the longest of the three.
6 Fairy Costume
Who wouldn’t love to have Alyssa Milano as their fairy godmother? The 5-foot-2 stunner dazzles the red carpet at this high-profile costume party. Her fairy outfit manages to look fun, and a tad bit sexy as well. That being said, one gets the impression that Milano could walk around in a garbage back and still look nothing short of phenomenal. The actress may not have gotten carried away with the outfit but, from the looks of things, she may be able to fly away in it.
Milano Moment: After a roughly one-year long courtship, Alyssa Milano became engaged to a talent agent named Dave Bugliari back in December of 2008. They made it official on August 15, 2009, and they are still married to this day.
This is a promo photo of Milano portraying the role of Phoebe Halliwell in the hit television show Charmed. The gorgeous performer looks unsurprisingly amazing in this particular shot. Interestingly enough, the role was originally supposed to be played by actress, Lori Rom. However, Rom quit the show, and a new pilot episode was filmed with Milano stepping in to take her place. Her character was the most free-spirited of the three Halliwell sisters. Alyssa Milano turned out to be an excellent choice for the role, which she played for eight seasons.
Milano Moment: The WB series Charmed first aired on October 7, 1998, and ended in May of 2006. It received above average reviews and was the network's second most popular show for the first three seasons of it’s run.
4 All Blue Everything
It seems like Alyssa Milano enjoys posting throwback photos on her Instagram feed, almost as much as her fans like seeing them. The busty television star can be seen modeling a see-through blue top which helps to draw attention to her prominent upper half. The former child star knows how to keep her fan base engaged, based on the well over 10,000 likes on Instagram that this photo received. The actress reminds us, yet again, why she is worth a follow on social media sites like Instagram.
Milano Moment: Some fans may not realize that Milano has dyslexia. In a quote from abstracts.net, she stated “I've stumbled over words while reading from teleprompters. Sir John Gielgud, whom I worked with years ago, gave me great advice. When I asked how he memorized his monologues, he said, "I write them down." I use that method to this day.”
3 Dressed In Black
Alyssa Milano gives us her best biker chick look in this memorable photograph. The movie star shows us a bit of her rebellious side with this all black get up. There are likely several male bikers who would love to travel the open road with this Hollywood babe on the back of their motorcycle. After seeing this photo, one could make the argument that dressing in all-black attire might just be the perfect look for the 44-year-old television icon.
Milano Moment: Some casual fans may not be an aware that Milano released four music albums between 1989 to 1992. While the albums weren’t big in the States, the bubblegum pop records were a commercial success in Japan. Milano has since expressed her displeasure with the albums' musical quality.
2 The Cast
This Instagram post features the three lovely stars from the hit show, Charmed; Alyssa Milano, Shannen Doherty, and Holly Maire Combs. As one can ascertain from this image, the cast featured some of the hottest women in television at the time. This fun throwback photo was understandably popular amongst Milano’s Instagram followers and received well over 67,000 likes. Pics such as this one are a big part of the reason that Alyssa Milano has such a huge following on social media outlets like Instagram. This image will likely bring back fond memories for fans of the show.
Milano Moment: The first episode of Charmed was seen by an eye-popping 7.7 million viewers. The popular WB series, which ended back in 2006, still has something of a cult following to this day.
This article features a number of Alyssa Milano’s best throwback photos. That being said none of the pics throw quite as far back as this one. In this image, we see a young Milano posing for the camera in red leather pants and a top that exposes her midsection. Based on the poster for the film Feeling Minnesota in the background, we can assume this photo was taken sometime around 1996 (the year the movie was released). It may be hard for longtime fans to believe that this picture was likely taken over two decades ago.
Milano Moment: Back in 2013, Milano created her very own comic book series called Hacktivist. The series is described as a cyber-thriller that focuses on modern hacking and global activism.
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