It was a controversial decision, but they clearly wanted to make a statement with her haircut :lol:

To tell you the truth, if I didn't know who Alyssa Milano was and I had never seen Who's the Boss? prior to Season 7, I would say that she was still a pretty young woman. I mean, Alyssa later sported really short hair (https://www.youtube.com/watch?v=Zh2D7teY6SM) on Charmed (https://www.therichest.com/world-entertainment/15-times-alyssa-milano-was-everyones-favorite-charmed-one/) (in its sixth season (https://www.google.com/search?q=charmed+season+6+alyssa+milano&tbm=isch&ved=2ahUKEwigpePN4Lj3AhXhmmoFHWnECu0Q2-cCegQIABAA&oq=charmed+season+6+alyssa+milano&gs_lcp=CgNpbWcQAzoECAAQQzoFCAAQgAQ6BggAEAcQHjoECAAQHjoGCAAQBRAeUK0DWMgeYP4haAFwAHgCgAHIBogB5yGSAQ0wLjkuMS4yLjIuMC4xmAEAoAEBqgELZ3dzLXdpei1pbWfAAQE&sclient=img&ei=b5RrYuCxOOG1qtsP6Yir6A4&bih=789&biw=1600)), and somehow made it work (https://i.pinimg.com/originals/af/95/f7/af95f7b3664618ac77ae87a939aaf8a9.jpg). Maybe part of it is because Alyssa was by that point, a lot older and the short-hair didn't seem to drastically "age" her as much as it did on Who's the Boss?

https://c8.alamy.com/comp/B84H3E/charmed-tv-series-1998-2006-usa-2004-season-6-episode-17-hyde-school-B84H3E.jpg

And maybe it was too jarring to see Alyssa with short-hair on Who's the Boss? because it wasn't that long ago, that her hair was really long and thick, and like I said before, that was to me, when Alyssa was at her prettiest as Samantha Micelli:
https://media.gettyimages.com/id/93741561/photo/who-s-the-boss.jpg?s=1024x1024&w=gi&k=20&c=GDCG18TKl1ky_f6aRa7_Tgu5RovvCfFXh2HntX6QEOs=

Sam with short-hair pretty much coincides with Who's the Boss? really declining in quality beginning in Season 7.

Oh totally! She looks amazing with short hair, especially in that pic you posted. But my God they were clearly going for a look that would make her look boyish and dowdy and remove the sexiness.

GAC Family is currently in the middle of Season 7 of their recent cycle and I never realized how decidedly unflattering that short hair style looked on Alyssa Milano until rewatching the episodes. I don't know how to explain it but not only does she just gives off this dowdy, unsexy, and boyish vibe, but also an "old vibe". She kind of to me, looks like Moe Howard (https://r.search.yahoo.com/_ylt=AwrOp8ufZRljmSMH0U5XNyoA;_ylu=Y29sbwNncTEEcG9zAzEEdnRpZAMEc2VjA3Ny/RV=2/RE=1662637599/RO=10/RU=https%3a%2f%2fen.wikipedia.org%2fwiki%2fMoe_Howard/RK=2/RS=YO_p.YH5RpHfS89IfOumrhEdH18-) with the dark bowl-like cut.

https://static.tvmaze.com/uploads/images/large_landscape/308/771406.jpg

They bring Sam's best friend Bonnie back for one final episode (http://reviewingeverytvshowiown.blogspot.com/2017/05/whos-boss-you-can-go-home-again.html) and Sam gives off the impression that she's more like Bonnie's aunt than her peer. I suppose that the short hairstyle and some of the clothes that Sam wore gave her a middle-age, unhip, soccer mom vibe.

There isn't a woman alive that could make that haircut look good.

There isn't a woman alive that could make that haircut look good.

Alyssa just posted this on Instagram (https://www.instagram.com/p/CiQMr7EpqIS/?hl=en) of her in Teen Beat magazine from back in the day. This to me, further drives home the point that Alyssa on Who's the Boss? looked better and her best with long, medium brown/slightly blondish hair.

https://pbs.twimg.com/media/CLLpzJqW8AAdM6c.jpg

Oh totally! She looks amazing with short hair, especially in that pic you posted. But my God they were clearly going for a look that would make her look boyish and dowdy and remove the sexiness.

I wonder what compelled Alyssa to radically change her look towards the end of the series? I've said this before, but I can't get over how insanely beautiful Alyssa looked in the "In Search of Tony" episode at the start of Season 6.

I remember hearing(i can't recall on what show, but it was definitely on the E! network, so had to be a True Hollywood Story/Behind the Scenes of Who's The Boss type) that Alyssa attempted to get out of her contract early. The Powers That Be said "No" so I'm wondering if maybe the haircut was a bit of revenge/"would they fire me over this?" wishful thinking.

I remember hearing(i can't recall on what show, but it was definitely on the E! network, so had to be a True Hollywood Story/Behind the Scenes of Who's The Boss type) that Alyssa attempted to get out of her contract early. The Powers That Be said "No" so I'm wondering if maybe the haircut was a bit of revenge/"would they fire me over this?" wishful thinking.

I know that shortly after Who's the Boss? went off the air in 1992, Alyssa just about took on the most raunchy, most non-family friendly roles (https://www.nydailynews.com/q-tv-kid-turned-movie-star-alyssa-milano-article-1.717812) that she could get her hands on like Embrace of the Vampire, Poison Ivy II (https://movieadayblog.wordpress.com/2016/10/27/october-27th-2016-movie-poison-ivy-ii-lily/), and a made for TV movie about the Amy Fisher saga. Basically, anything that showed that she wasn't Tony Danza's TV daughter anymore and she was "all grown up (https://www.thehairpin.com/2017/12/watching-alyssa-milano-grow-up/)". There's even an article called "The Five Trashiest Alyssa Milano Movies Ever Made", which I don't want to link out of fear that it's not "safe for work".

I remember hearing(i can't recall on what show, but it was definitely on the E! network, so had to be a True Hollywood Story/Behind the Scenes of Who's The Boss type) that Alyssa attempted to get out of her contract early. The Powers That Be said "No" so I'm wondering if maybe the haircut was a bit of revenge/"would they fire me over this?" wishful thinking.

Alyssa according to this blog post (http://popcultureaddictlifeguide.blogspot.com/2012/06/whos-boss.html), wanted to leave the show at the end of the seventh season to go to college, but because she was still under contract, she had to stay on throughout the eighth season (which ended up being the last one).

There isn't a woman alive that could make that haircut look good.

I was reminded of this again, when I saw on IFC the last few episodes of Season 7, namely "Between a Rock and a Hard Place" (http://reviewingeverytvshowiown.blogspot.com/2017/05/whos-boss-between-rock-and-hard-place.html) and the "Road to Washington" two parter. Alyssa Milano had that I would call "May I speak to your manager!?" haircut (https://www.google.com/search?sxsrf=APwXEde2_P5pU2rHt-9hWCiWrZezCQMRDA:1688110256540&q=Karen+haircut&tbm=isch&sa=X&ved=2ahUKEwjR5LrhvOr_AhVjl4kEHRnzBkAQ0pQJegQIDBAB). Maybe whenever I see Sam with super short hair, it's a perfect indicator that I'm watching a post-jump the shark (https://www.sitcomsonline.com/boards/showthread.php?p=6135671) episode of Who's the Boss?

https://static1.purepeople.com/articles/9/86/37/9/@/687700-l-actrice-alyssa-milano-a-18-ans-en-580x0-3.jpg

https://www.picclickimg.com/I8MAAOSwYAFkSo27/TV-Hits-MAGAZINE-June-1991-Alyssa-Milano-Madonna.webp

Alyssa Milano had that I would call "May I speak to your manager!?"haircut.

Genuine lol at this observation, I cannot stand that hair cut on such a beautiful face! Whenever I re-watch the series I have two specific moments that make me actually sad that the show is nearly "over":

#1) She dyes her hair nearly jet black
#2) The godawful short haircut (more brutal than #1, but #1 happens first)

Genuine lol at this observation, I cannot stand that hair cut on such a beautiful face! Whenever I re-watch the series I have two specific moments that make me actually sad that the show is nearly "over":

#1) She dyes her hair nearly jet black
#2) The godawful short haircut (more brutal than #1, but #1 happens first)

I recently watched this video (https://www.youtube.com/watch?v=mi1FyzQxvyo) on Home Improvement, and in it, the latter seasons, specifically Seasons 7 and 8 are labeled (https://youtu.be/mi1FyzQxvyo?t=739) as the "kitchen sink" seasons. A "kitchen sink" season or year is when it becomes very obvious that a show is trying any idea possible to maintain viewers' interest.

I would say that Sam dying her hair nearly jet black half way into Season 6 was the beginning point if you will, of Who's the Boss' own "kitchen sink" years. Shortly there after, came the "Sam Accelerates" episode, where Sam is out of the blue, offered a chance to graduate from high school early. I've stated before, that it never made sense given Samantha's prior academic history, that she was a good enough of a student to be able to graduate a year ahead of time.

The following season, came the introduction of Billy and Sam's cowboy love interest Matt. It seemed like they were setting Matt up to be a semi-regular character and foil to Tony, but he was gone well before the season was up and never seen or mentioned after that. Sam's rushed courtship and marriage to Hank in the final season, is probably the ultimate example of Who's the Boss? throwing things at the wall and seeing what will stick.

I remember hearing(i can't recall on what show, but it was definitely on the E! network, so had to be a True Hollywood Story/Behind the Scenes of Who's The Boss type) that Alyssa attempted to get out of her contract early. The Powers That Be said "No" so I'm wondering if maybe the haircut was a bit of revenge/"would they fire me over this?" wishful thinking.

Alyssa was apparently up for (https://www.notstarring.com/actors/milano-alyssa) the Juliette Lewis role (http://kent-informationoverload.blogspot.com/2010/09/72-cape-fear-1991.html) in Cape Fear (https://www.imdb.com/title/tt0101540/trivia/?ref_=tttr_ql_trv_1) (a role that ultimately earned Juliette an Academy Award nomination for Best Supporting Actress) but Tony Danza pressured her (https://tvtropes.org/pmwiki/pmwiki.php/Trivia/CapeFear) to turn it down. Now, Alyssa was asked (https://www.reddit.com/r/IAmA/comments/2d00ip/comment/cjkpluq/?utm_source=reddit&utm_medium=web2x&context=3) if this was true, and she claims (https://www.reddit.com/r/IAmA/comments/2d00ip/comment/cjkqewt/?utm_source=reddit&utm_medium=web2x&context=3) that it isn't.

It was a controversial decision, but they clearly wanted to make a statement with her haircut :lol:

C10wB3Jonys

To impress a girl, Jonathan uses Tony's car and scratches it.

From Season 7 Episode 14, 'Days of Blunder'. Jonathan uses Tony's prized Jeep to impress a girl and returns it with a large scratch.

Genuine lol at this observation, I cannot stand that hair cut on such a beautiful face! Whenever I re-watch the series I have two specific moments that make me actually sad that the show is nearly "over":

#1) She dyes her hair nearly jet black
#2) The godawful short haircut (more brutal than #1, but #1 happens first)

As others have pointed out (https://www.youtube.com/watch?v=TZOcLM5NVbY&lc=UgzmkS6kSbkhQxjyRjV4AaABAg) in the comments section of this video, Sam with short hair coincides with her character becoming decidedly less likable (https://www.youtube.com/watch?v=TZOcLM5NVbY&lc=UgwpQ8M7LzTlqgk-56J4AaABAg) and appealing:
TZOcLM5NVbY

People want a change now and then. I think she wanted to go with a shorter cut or bob.

I've never had long hair, but my wife had beautiful hair. It took a lot of time and effort to maintain the look and style. She grew tired of the hassle and asked if me if she could cut it. And you know what? I agreed to her cutting it short and I loved her no less.

I think it was good for Alyssa to make a change. She probably needed to have a different hairstyle at that point of her life.

People want a change now and then. I think she wanted to go with a shorter cut or bob.

I've never had long hair, but my wife had beautiful hair. It took a lot of time and effort to maintain the look and style. She grew tired of the hassle and asked if me if she could cut it. And you know what? I agreed to her cutting it short and I loved her no less.

I think it was good for Alyssa to make a change. She probably needed to have a different hairstyle at that point of her life.

This is my personal opinion, but I think that Alyssa's hairstyle in the first season of Charmed was a more cute and flattering version of a shorter cut or bob on her than when compared to the latter years of Who's the Boss?

https://images2.fanpop.com/image/photos/12800000/Thank-You-For-Not-Morphing-charmed-12812137-1280-960.jpg

https://i.redd.it/7b94fe7125r71.jpg

https://i.pinimg.com/736x/ef/8b/f3/ef8bf3ac4a25078f480f828ce32e9758.jpg

Like I said, it seemed like Alyssa come 1990-91, was jumping on the trend of women getting that layered, butch haircut (see for example, Demi Moore in the film Ghost, Chynna Phillips (https://www.sitcomsonline.com/boards/showpost.php?p=6040102&postcount=21) of Wilson-Phillips, Dana Delany (https://www.sitcomsonline.com/boards/showpost.php?p=6194401&postcount=39) on China Beach, Bridget Fonda in the film Single White Female, Janine Turner on Northern Exposure, Josie Bissett on Melrose Place, Debbie Gibson (https://www.instagram.com/p/CzlCPP9u6KL/?next=%2F&e=7ad556e5-8b9f-4bd9-85bf-73f46df8fec6&g=5), etc.).

I was reminded of this again, when I saw on IFC the last few episodes of Season 7, namely "Between a Rock and a Hard Place" (http://reviewingeverytvshowiown.blogspot.com/2017/05/whos-boss-between-rock-and-hard-place.html) and the "Road to Washington" two parter. Alyssa Milano had that I would call "May I speak to your manager!?" haircut (https://www.google.com/search?sxsrf=APwXEde2_P5pU2rHt-9hWCiWrZezCQMRDA:1688110256540&q=Karen+haircut&tbm=isch&sa=X&ved=2ahUKEwjR5LrhvOr_AhVjl4kEHRnzBkAQ0pQJegQIDBAB). Maybe whenever I see Sam with super short hair, it's a perfect indicator that I'm watching a post-jump the shark (https://www.sitcomsonline.com/boards/showthread.php?p=6135671) episode of Who's the Boss?

https://static1.purepeople.com/articles/9/86/37/9/@/687700-l-actrice-alyssa-milano-a-18-ans-en-580x0-3.jpg

https://www.picclickimg.com/I8MAAOSwYAFkSo27/TV-Hits-MAGAZINE-June-1991-Alyssa-Milano-Madonna.webp

Come to think of it, Alyssa from this time period with that dark and short hairstyle kind of looks like Martika (https://www.google.com/search?q=martika+&tbm=isch&ved=2ahUKEwi1x6bvm66CAxX0DWIAHS92AWoQ2-cCegQIABAA&oq=martika+&gs_lcp=CgNpbWcQAzIHCAAQigUQQzIFCAAQgAQyBQgAEIAEMgQIABAeMgQIABAeMgcIABAYEIAEMgcIABAYEIAEMgcIABAYEIAEMgcIABAYEIAEMgcIABAYEIAEUJISWJISYJ8VaABwAHgAgAGQCYgBkAmSAQM3LTGYAQCgAQGqAQtnd3Mtd2l6LWltZ8ABAQ&sclient=img&ei=vkBIZbXwGfSbiLMPr-yF0AY), who was on Kids Incorporated and had a #1 single (https://www.stereogum.com/2155704/the-number-ones-martikas-toy-soldiers/columns/the-number-ones/) in 1989 with Toy Soldiers (https://youtu.be/LvdLovAaYzM?list=RDgIbw0OkC9po).

https://cdn.suruga-ya.com/database/pics_light/game/250030772.jpg

People want a change now and then. I think she wanted to go with a shorter cut or bob.

I've never had long hair, but my wife had beautiful hair. It took a lot of time and effort to maintain the look and style. She grew tired of the hassle and asked if me if she could cut it. And you know what? I agreed to her cutting it short and I loved her no less.

I think it was good for Alyssa to make a change. She probably needed to have a different hairstyle at that point of her life.

Alyssa Milano's future Charmed co-star, Kaley Cuoco also you could say, infamously cut her hair short (https://people.com/style/kaley-cuoco-calls-her-big-bang-theory-pixie-cut-the-worst-decision/) and sported it (https://www.reddit.com/r/bigbangtheory/comments/ik1vq8/pennys_hair_cut_is_too_much_unsettling_for_me_for/) for about a season (https://www.looper.com/1146265/kaley-cuoco-quickly-regretted-pennys-pixie-cut-in-the-big-bang-theory-season-8/) on The Big Bang Theory (https://screenrant.com/big-bang-theory-penny-kaley-cuoco-short-haircut-explained/). It ultimately had the same effect that Alyssa's really short-hair during the last few seasons of Who's the Boss? had, in that it drastically or dramatically aged her:
https://media.glamour.com/photos/63405a5ae59925eab7e41b3a/master/w_1600,c_limit/kayley2.png

She sort of gave me Sandy Duncan vibes with that pixie cut.

It was a controversial decision, but they clearly wanted to make a statement with her haircut :lol:

This reminds me of this article that I just came across:
12 Gorgeous Celeb Looks That Were Ruined With A Hairstyle (https://www.thelist.com/1552535/celebrity-looks-ruined-with-hairstyle/)

No matter how beautiful the dress, sometimes our hairstyle or haircut is the element that makes or breaks an look, and celebrities certainly aren't immune.

Alyssa Milano's future Charmed co-star, Kaley Cuoco also you could say, infamously cut her hair short (https://people.com/style/kaley-cuoco-calls-her-big-bang-theory-pixie-cut-the-worst-decision/) and sported it (https://www.reddit.com/r/bigbangtheory/comments/ik1vq8/pennys_hair_cut_is_too_much_unsettling_for_me_for/) for about a season (https://www.looper.com/1146265/kaley-cuoco-quickly-regretted-pennys-pixie-cut-in-the-big-bang-theory-season-8/) on The Big Bang Theory (https://screenrant.com/big-bang-theory-penny-kaley-cuoco-short-haircut-explained/). It ultimately had the same effect that Alyssa's really short-hair during the last few seasons of Who's the Boss? had, in that it drastically or dramatically aged her:
https://media.glamour.com/photos/63405a5ae59925eab7e41b3a/master/w_1600,c_limit/kayley2.png

She sort of gave me Sandy Duncan vibes with that pixie cut.

Oh wow I never watched the show but that haircut looks so bad on her! She looks so vibrant and youthful in the left picture, in the right pic she looks like a 40 something divorcee (still very pretty though, not saying she's unattractive!)

This reminds me of this article that I just came across:
12 Gorgeous Celeb Looks That Were Ruined With A Hairstyle (https://www.thelist.com/1552535/celebrity-looks-ruined-with-hairstyle/)

Wow so many bad haircuts in that list! Madonna is easily the worst, but Juliette Lewis' cornrows are a close #2!

Oh wow I never watched the show but that haircut looks so bad on her! She looks so vibrant and youthful in the left picture, in the right pic she looks like a 40 something divorcee (still very pretty though, not saying she's unattractive!)

u6lp_PoIS0o

When women in the limelight get a pixie cut, it invariably comes under scrutiny. Why does society react so strongly to women having a pixie cut?

u6lp_PoIS0o

This is obviously, a subjective question, but is there any woman that you can think of who still seemed remotely "desirable" (i.e. she didn't look too "matronly" or "butch") despite having a super-short pixie haircut? I guess that Janine Turner (https://www.alamy.com/stock-photo-northern-exposure-janine-turner-1990-1995-cbscourtesy-everett-collection-128533365.html) when she was on Northern Exposure and in the movie, Cliffhanger (https://static0.colliderimages.com/wordpress/wp-content/uploads/2023/05/janine-turner-as-ranger-jessica-jessie-deighan-in-cliffhanger.png?q=50&fit=crop&w=825&dpr=1.5) is the first person to come to my mind:
https://images.squarespace-cdn.com/content/v1/53f0dc19e4b042bb7cb6e377/b7a0358c-2caf-4f70-9a24-e9f70679a29d/janine_turner_northern_exposure_.jpg.jpg

https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcS6xiZ-6AMEAHSL3F231cKTEmEUnTu3_ssvfw&s

https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcR4ycD_1YMHhrCY0zBa2SSI8TNsPPzpXDUG8Q&s

C38Pu2JOOrc