Alyssa Milano's hair during the fifth and sixth seasons [Archive] - Sitcoms Online Message Boards

TMC

01-17-2022, 06:24 AM

Did anybody else think that this was in essence, when her beauty peaked and blossomed on the show (https://www.youtube.com/watch?v=gKhCP6Qoac8)?

https://media.gettyimages.com/photos/in-search-of-tony-season-six-91989-samantha-mona-jonathan-angela-and-picture-id93741561?s=2048x2048

https://www.imago-images.com/bild/st/0100016908/w.jpg

https://walter.trakt.tv/images/episodes/000/039/638/screenshots/thumb/b2efb114ae.jpg.webp

https://flxt.tmsimg.com/assets/p7895024_i_h9_aa.jpg

I wonder if this particular look was the main inspiration for Disney modeling Ariel in The Little Mermaid after her.

I frankly, didn't like it when Alyssa cut her hair during the last few years of the show to a Dorothy Hamill-esque wedge. I suppose that it kind of aged her if that makes sense.

https://i.ytimg.com/vi/Y35GKXk0OG0/hqdefault.jpg?sqp=-oaymwEjCNACELwBSFryq4qpAxUIARUAAAAAGAElAADIQj0AgKJDeAE=&rs=AOn4CLAmFkNzttDyMRdSK8CT8kOWrQkcBw

Novera

01-20-2022, 06:06 PM

TMC

01-21-2022, 05:03 AM

TMC

02-11-2022, 05:36 AM

Novera

02-14-2022, 03:36 PM

I seriously wonder if there was any sort of outrage over Alyssa cutting her hair (a la what happened with Keri Russell when she cut her hair while doing Felicity) really short in the last two seasons of the show.

First of all I couldn't agree with you more on everything you said - and that picture of her in Jamaica is how my brain references her at all times. Like even today I like to imagine her that way, because I remember she was seriously the hottest thing that every guy I knew had ever seen at the time.

Also I remember the writers seemed to go out of their way to have Tony reference her darker hair ("you didn't clear that with me" or something to that effect). So I wonder if it's something Milano wanted, like she didn't want to be the sexy girl with long hair anymore. I recall Becky from Roseanne wanted a shorter hair cut but the producers said "no you're from a small town and you're poor, you should have normal long blond hair". So Roseanne grabbed a pair of scissors and cut out a chunk of her hair, forcing them to give her one of those early 90s bob cuts.

Boy George went through a similar thing in the mid 80s when he said he began to feel like a doll, so he cut off his hair with that "chopped up" black hair cut that was featured in their 1986 album cover.

But at the same time it would be totally possible that the network was like "ok she's being too sexy, lets make her more wholesome"... but I can't imagine they'd do that when their market research would've shown she has reached iconic status among teen boys (Italian or otherwise!)

rusty spike

02-14-2022, 05:53 PM

Novera

02-15-2022, 07:32 PM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

That's actually a good point, because I'm re-visiting that era through the eyes of a modern era. But back then a short bob cut would've been a hot/fresh/new cut to show off. After 10 years of long hair, that was new and fun!

MikeLutton

02-15-2022, 10:11 PM

i alway's thought sam had nice hair 2 once she got older,

TMC

02-15-2022, 11:39 PM

First of all I couldn't agree with you more on everything you said - and that picture of her in Jamaica is how my brain references her at all times. Like even today I like to imagine her that way, because I remember she was seriously the hottest thing that every guy I knew had ever seen at the time.

Also I remember the writers seemed to go out of their way to have Tony reference her darker hair ("you didn't clear that with me" or something to that effect). So I wonder if it's something Milano wanted, like she didn't want to be the sexy girl with long hair anymore. I recall Becky from Roseanne wanted a shorter hair cut but the producers said "no you're from a small town and you're poor, you should have normal long blond hair". So Roseanne grabbed a pair of scissors and cut out a chunk of her hair, forcing them to give her one of those early 90s bob cuts.

Boy George went through a similar thing in the mid 80s when he said he began to feel like a doll, so he cut off his hair with that "chopped up" black hair cut that was featured in their 1986 album cover.

But at the same time it would be totally possible that the network was like "ok she's being too sexy, lets make her more wholesome"... but I can't imagine they'd do that when their market research would've shown she has reached iconic status among teen boys (Italian or otherwise!)

I'm assuming that this was also around the same time that Alyssa did a photoshoot while wearing a New Jersey Devils jersey:
http://images6.fanpop.com/image/photos/37500000/Teen-Pinup-alyssa-milano-37580279-564-765.jpg

https://i.pinimg.com/originals/4d/24/53/4d24531481c882d6977b4a043cae7bf4.jpg

https://i.pinimg.com/originals/47/4c/43/474c4344d44b617bb8190bc9f4bc4e61.jpg

https://w0.peakpx.com/wallpaper/742/150/HD-wallpaper-alyssa-the-devil-new-jersey-devils-alyssa-milano-nhl-sexy-alyssa.jpg

https://thumbs.worthpoint.com/zoom/images1/1/0612/04/alyssa-milano-jersey-devils-poster_1_6c6d940b4e787ae1b767d64001f504f7.jpg

https://i.pinimg.com/736x/e1/3c/72/e13c7269882190ad47fe7034406d1da8.jpg

I guess that I would label this the "Teen Steam" era, since it was also around that same time that Alyssa's "infamous" (https://ohnotheydidnt.livejournal.com/78581045.html) workout (https://www.throwbacks.com/alyssa-milanos-shares-memories-from-teen-steam-workout-video-2/) video (https://tvovermind.com/how-the-classic-alyssa-milano-80s-teen-steam-video-came-to-be/) of the same name was released.

TMC

02-19-2022, 02:57 AM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

Interestingly, this is what I dug up on the old Jump the Shark (https://web.archive.org/web/20061031122842/http://www.jumptheshark.com/w/whostheboss.htm) website:

Everyone agrees sam was a babe but what about that harsh faze where she cut off her hair, gained weight, and started wearing work out clothes around the house constantly? harsh 80's jane fonda type leotards, wrist bands headband, the whole deal. she looked awful and she started acting weird around that time too, REALLY pleased with herself i think she was suppose to be working in a gym or owned it or something. yick. then she shacked up with some loser and tony couldn't do a thing about it because she was of age. so cute daughter just barely under her dad's worried thumb went out the door in a big way. SHARK! what happened?! she was so cute before and so un-full-of-herself! puberty was great for her, young adulthood killed her character! she looks great now by the way...

I loved the show up unto the point where Samantha chopped off her hair. After that, everything she wore was just dark and goth. I liked the more cutesy dressed, curly brown-haired Sam. Her dark, straight hair ruined it for me. I use to watch the show to check out her hair and clothes. I couldn't depend on her anymore for fashion tips.

When Sam after college moved to work in some country inn and met her new man. She had short hair and was always working behind the counter when they showed her. That's when the new kid, Billy joined the show. It was never the same.

Who's the Boss jumped the shark when Tony and Angela got together because this undermined the whole premise of the show....the tension and anticipation was gone. It also was nearing rocky waters once the kids got to be teenagers, Sam cut her hair and Billy (hah???) was introduced. You are what you surround yourself with and Katherine Helmond, Judith Light and Tony Danza were surrounded by some stuff that was dragging them down!!!!

It definitely jumped the shark when Jonathan and Sam had the exact same haircut! Sam had the dark wedge and Jonathan had the blonde wedge! At first I thought they were Ann & Nancy Wilson from Heart, but soon realized that it was just Alyssa and Jonathan!

When Alyssa Milano dyed her hair black and cut it shoulder length. I hung in there until she chopped it all off. That was the final straw. Alas, the cutting of her hair tied in with her skipping grades, which was a bad move. Lost all teenage viewers at that point.

TMC

03-03-2022, 04:11 AM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

To tell you the truth with the recent benefit of Who's the Boss? airing constantly on GAC Family, Sam's drastic change in her hairstyle is around the time that I really start to lose interest in the show. What I mean is that Sam with short-hair pretty much coincides with the big "shark jumping" moments of the show like Tony and Angela officially getting together, Tony and Mona's characters arguably undergoing severe cases of Flanderization, the introduction of Billy, and Sam's rushed marriage to Hank.

And maybe the petty and shallow part in me says that Alyssa Milano was "messing with perfection" because she was arguably the most beautiful that she had ever looked come the start of Season 6 and the Jamaica episode. And I do suspect that a lot of teen viewers (especially boys) were turned off by Sam's abrupt maturity/evolution in the last few years of the show.

https://m.media-amazon.com/images/I/51zIhxuCrKL._AC_.jpg

https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcRhTIGTxBjNQoaakLvER9A74vtBXYrUSqDK7Q&usqp=CAU

https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcRkIqMQLKRS6tiwltGiSjNzqzVCLG-RAUZDyg&usqp=CAU

https://sanet.pics/storage-6/1120/1AoDGcWNRfGHEiygFwWeOoMarkMgeSzr.jpg

TMC

03-09-2022, 06:06 AM

Another photo (https://www.instagram.com/p/Ca2sLiEFKaB/) of Alyssa (https://www.instagram.com/p/CJq9Hh_nGtN/) during her "long and luxurious brown hair" days (https://www.instagram.com/p/CFp9tk_nWri/) on WTB.

TMC

03-10-2022, 04:50 AM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

I know that I'm speculating, but I wonder if Alyssa cut her hair in part because she was worried about being too "sexualized". That was the argument that her Charmed co-star turned "frenemy" (https://www.news.com.au/entertainment/celebrity-life/rose-mcgowan-accuses-charmed-costar-alyssa-milano-of-being-a-metoo-fraud/news-story/aeb7a88167428ee04051b7000ecce48f) Rose McGowan had (https://www.dailymail.co.uk/tvshowbiz/article-4625666/Rose-McGowan-reveals-shaved-hair-off.html) for why she cut off (https://www.irishnews.com/magazine/entertainment/2020/01/03/news/rose-mcgowan-reveals-why-short-hair-could-have-cost-her-acting-jobs-1804616/) her hair. And many guys (https://www.youtube.com/watch?v=DxkEU0PqFvM) back in the day (https://screenrant.com/guardians-galaxy-movie-ship-alyssa-milano-reaction-response/), did have huge (https://www.usmagazine.com/celebrity-news/news/channing-tatum-reveals-childhood-crush-on-alyssa-milano-she-was-it-man-201337/) crushes (https://www.amongmen.com/women-relationships/high-school-crushes-alyssa-milano/) on Alyssa Milano (https://www.dailymail.co.uk/video/tvshowbiz/video-1363305/Justin-Timberlake-reveals-Alyssa-Milano-childhood-crush.html) and saw her as kind of their dream girl.

Also, Alyssa did claim that she, around the time that she was doing Who's the Boss? was (https://www.yahoo.com/video/alyssa-milano-reveals-details-about-a-second-sexual-assault-when-she-was-24-im-not-really-ready-to-expose-that-human-161839804.html) sexually assaulted (https://www.usatoday.com/story/life/people/2018/10/05/alyssa-milano-concert-sexual-assault-19-punched-metoo/1532125002/). So maybe, something like that goes hand in hand.

TMC

03-10-2022, 06:37 AM

TMC

03-10-2022, 11:24 PM

First of all I couldn't agree with you more on everything you said - and that picture of her in Jamaica is how my brain references her at all times. Like even today I like to imagine her that way, because I remember she was seriously the hottest thing that every guy I knew had ever seen at the time.

Also I remember the writers seemed to go out of their way to have Tony reference her darker hair ("you didn't clear that with me" or something to that effect). So I wonder if it's something Milano wanted, like she didn't want to be the sexy girl with long hair anymore. I recall Becky from Roseanne wanted a shorter hair cut but the producers said "no you're from a small town and you're poor, you should have normal long blond hair". So Roseanne grabbed a pair of scissors and cut out a chunk of her hair, forcing them to give her one of those early 90s bob cuts.

Boy George went through a similar thing in the mid 80s when he said he began to feel like a doll, so he cut off his hair with that "chopped up" black hair cut that was featured in their 1986 album cover.

But at the same time it would be totally possible that the network was like "ok she's being too sexy, lets make her more wholesome"... but I can't imagine they'd do that when their market research would've shown she has reached iconic status among teen boys (Italian or otherwise!)

I just saw the episode that first featured Alyssa Milano's new jet black, "cut to the shoulders" hairstyle ("Supermom Burnout" (https://player.fm/series/ay-oh-oh-ay-the-whos-the-boss-podcast/supermom-burnout)) on GAC Family. There's a scene in the kitchen early on where Jonathan is teasing Sam about her hair looking like an oil slick. And that's when Tony had a reference about her hair color now being darker. I'm assuming that was to get it out of the way because they figured the audience were going to say something about Sam's hair suddenly looking different in the middle of the season.

TMC

03-17-2022, 05:09 AM

i alway's thought sam had nice hair 2 once she got older,

I've brought up the "In Search of Tony" episode but I just remembered that Sam's hair also looked magnificent in the "Your Grandmother's a Bimbo" (https://podcasts.apple.com/us/podcast/your-grandmothers-a-bimbo/id1528039547?i=1000532783496) episode from the season prior.

https://media.gettyimages.com/photos/your-grandmothers-a-bimbo-season-five-12989-in-his-bid-to-run-for-picture-id93741623?s=2048x2048

biffbronson

03-17-2022, 09:23 AM

WOW -- that's the longest I've seen her hair. Pretty color.

TMC

03-27-2022, 03:26 AM

That's actually a good point, because I'm re-visiting that era through the eyes of a modern era. But back then a short bob cut would've been a hot/fresh/new cut to show off. After 10 years of long hair, that was new and fun!

What's funny is that when Alyssa (https://tvtropes.org/pmwiki/pmwiki.php/Creator/AlyssaMilano) was doing Charmed (https://charmeddatabase.fandom.com/wiki/Phoebe%27s_Hairstyles), she had about sixth different (https://reelrundown.com/tv/The-HairVolution-Of-Phoebe-Halliwell-From-Charmed) hairstyle changes (https://www.reddit.com/r/charmed/comments/i9f354/best_lookhaircut_for_phoebe/) by the fourth season alone.

TMC

03-29-2022, 10:52 PM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

Come to think of it, I kind of reminds me of Christina Applegate changing her style to presumably better align with the times on Married...with Children. This is what I wrote (https://www.sitcomsonline.com/boards/forumdisplay.php?f=84) about matter:
One comment (https://www.datalounge.com/thread/26574646-what-would-the-characters-of-%E2%80%9Cmarried...-with-children%E2%80%9D-be-up-to-in-the-2020s) that I read is that when Christina Applegate cut her hair shorter and began dressing more maturely during the last few seasons of MWC's peak, it marked a marked a sea change (https://web.archive.org/web/20061031121504/http://www.jumptheshark.com/m/marriedwithchildren.htm). I presume that this also coincided with the grudge movement displacing (https://loudwire.com/grunge-killed-ended-hair-metal/) hair metal.

In effect, when Kelly (https://lovetabii.wordpress.com/2014/06/04/retro-fashion-kelly-bundy/) sported long, tousled blond (https://www.moviefone.com/photos/11-reasons-kelly-bundy-from-married-with-children-is-a-true-90s-icon/) hair (https://www.huffpost.com/entry/christina-applegate-kelly-bundy-pictures_n_1504592), bright red lipstick, and "L.A. teen hooker (https://galoremag.com/flashback-fashion-friday-style-icon-kelly-bundy/) mall rat" clothes (http://nyloninfilm.com/index.php?title=Married_with_Children), that was when the show was truly great. It is though, kind of funny hearing Christina Applegate today say that she wouldn't want to revisit Kelly Bundy if it meant having to dress like that (https://www.youtube.com/watch?v=vP-xXFBEek4) again.

Also, compare the way that DJ Tanner looked in the early seasons of Full House, when '80s fashion and sensibilities were still prevalent, to the final few years in the mid-'90s. Candace Cameron also like Alyssa Milano circa Seasons 5-6 of Who's the Boss, had really long, medium brown, thick and nicely coifed hair in about the middle of Full House's run:
https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcTNhIb9tUjsxSIi1TDXu6oZ2Cr7cZ8EEPq788E98YNZFMA_ZX77lY0nLiyTrayM18D2-Ok&usqp=CAU

http://images6.fanpop.com/image/polls/1446000/1446079_1420247664679_full.jpg?v=1420248157

https://occ-0-2794-2219.1.nflxso.net/dnm/api/v6/9pS1daC2n6UGc3dUogvWIPMR_OU/AAAABbid66qxANnD3B6JV4M9IxncKJ0F7wiFf7iEQ0kpuGT2Ud00Eiz1d02F32PMXvHIn1yU5H0cmVUQTEoYfZoCp619xAgRBLWu9msooVK_v6n_1jS8.jpg?r=364

And then by the time that the show went off the air in 1994-95, Candace had cut her hair really short:
https://resizing.flixster.com/d67KpqKrITtd53IBze50RW4W9jw=/300x300/v2/https://flxt.tmsimg.com/assets/p1100166_e_h9_ab.jpg

https://i.pinimg.com/originals/10/dc/5d/10dc5d73a2696fee8190a29688c369ed.jpg

There's also the way that Kelly Taylor on Beverly Hills, 90210 looked in the early years (i.e. the Shannen Doherty/Brenda Walsh years) to later:
http://www.dlisted.com/files/kelllycomingback1.jpg

https://purewows3.imgix.net/images/articles/2019_05/jennie-garth-tori-spelling-soccer-mom-haircut.jpg?auto=format,compress&cs=strip

TMC

04-09-2022, 05:44 AM

WOW -- that's the longest I've seen her hair. Pretty color.

Some photos that I managed to capture off of CTV.ca from the "Double Dump" (https://i.postimg.cc/pv3WbytG/Who-s-the-Boss-S05-E06-Double-Dump-mkv.jpg) episode. Other than probably the "In Search of Tony" episode at the start of Season 6, this is probably where Alyssa Milano looked her most stunningly beautiful during her time on Who's the Boss?

https://i.ibb.co/zXzC6j4/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-19-04-2022-04-09-02-48-29.jpg

https://i.ibb.co/V06Zqzr/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-18-03-2022-04-09-02-47-38.jpg

https://i.ibb.co/8bCzNKk/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-16-13-2022-04-09-02-55-41.jpg

TMC

04-15-2022, 10:41 PM

Absolutely! This was the era where my brother painted his bedroom wall with magazine cut outs of her, he was absolutely obsessed. I remember the crop/bob cut being more popular in the early 90s (thanks to Demi in Ghost, Wilson Philips etc.) but it made her look dowdy or matronly... I can't put my finger on it, it just didn't work for her. I think my personal favourite/peak moment was when Al fixes up her hair ("with a DIFFUSAH") and she was peak late 80s/early 90s :)

It's funny that you bring up Wilson Philips, because I was today on GAC Family, watching an episode from the seventh season ("Between a Rock and a Hard Place" (http://reviewingeverytvshowiown.blogspot.com/2017/05/whos-boss-between-rock-and-hard-place.html)), where Sam is trying to book Wilson Phillips for a college event. Alyssa Milano had really short hair at that point, which kind of made her look like a dark-haired decoy of Chynna Phillips:
https://static.tvmaze.com/uploads/images/large_landscape/308/771416.jpg

https://s2.dmcdn.net/v/Ooo891Rn-s_D4_PNa/x1080

https://s2.dmcdn.net/v/LBFrR1PWWND5h1YeV/x1080

https://media.gettyimages.com/photos/american-singer-and-actress-chynna-phillips-of-the-american-pop-group-picture-id1355187200?s=612x612

https://celebposter.com/thumbs_mousepad/Chynna-Phillips-mousepad_2637512.jpg

Even though it came out almost five years after Who's the Boss? ended, Alyssa Milano oddly looked more "hip", attractive, and age appropriate in the film Fear (https://www.youtube.com/watch?v=H_XGzIYDbXM) than she did in the last two seasons of WTB. It likely helped that Alyssa by that point, wasn't styled like a soccer mom:
https://64.media.tumblr.com/50aa24b66c0fa2fbb777ec25e70fc570/0dd308a810a9c8d1-07/s1280x1920/e01b4e1d0556248667286aeaf125e5d74a246fda.jpg

https://i.imgur.com/aNJngVF.gif

https://pyxis.nymag.com/v1/imgs/850/15f/e3d931d0c247a59d2a5375f89efd2d2bdc-23-fear-belly-shirts3.2x.h473.w710.png

https://64.media.tumblr.com/48aeaba683ed1987f71725e4974aeaee/0dd308a810a9c8d1-2d/s1280x1920/7ff0962e5e2b8471f71c3639d0061ebfea1bb444.jpg

TMC

04-24-2022, 12:56 AM

WOW -- that's the longest I've seen her hair. Pretty color.

Alyssa kind of to me, looks similar to her Season 5-early Season 6 look in this photo from 2015 (https://www.etonline.com/news/171356_alyssa_milano_says_ex_boyfriend_justin_timberlake_and_britney_spears_were_super_love):
https://www.etonline.com/sites/default/files/styles/video_1280x720/public/images/2015-09/1280_ET_INTV_ALYSSA_MILANO_090415.jpg?itok=mECE3xiP

jHvX5kX_BJw

TMC

04-27-2022, 05:33 AM

That's actually a good point, because I'm re-visiting that era through the eyes of a modern era. But back then a short bob cut would've been a hot/fresh/new cut to show off. After 10 years of long hair, that was new and fun!

Come to think of it, Alyssa circa Season 5-early Season 6 of WTB kind of reminds me of Amy Willerton (https://en.wikipedia.org/wiki/Amy_Willerton) and her (https://www.instagram.com/missamywillerton/) own amazing head of hair:
http://assets.talentmanagement.com/blog/wp-uploads/2013/12/Amy-Willerton-is-naturally-beautiful-why-did-she-feel-the-need-to-bring-makeup-to-the-jungle.jpg

https://encrypted-tbn0.gstatic.com/images?q=tbn:ANd9GcQGxlc_u6EABFK6rmo46cB1pjXJRIE9zxYQlLN5ffa6Jkol8xYWRZ4qZQ0gGi1ubZxJYZ8&usqp=CAU

https://i2-prod.dailystar.co.uk/incoming/article18473322.ece/ALTERNATES/s1200c/51642

https://i2-prod.dailystar.co.uk/incoming/article18492391.ece/ALTERNATES/s1200c/51184

lolzryFWF_4

TMC

06-01-2022, 05:40 AM

WOW -- that's the longest I've seen her hair. Pretty color.

I just remembered that I also liked the way that Sam/Alyssa's hair was styled (somewhat wavy) and looked in the "Life's a Ditch" (https://podcasts.apple.com/us/podcast/lifes-a-ditch/id1528039547?i=1000543343849) episode (the official backdoor pilot to Living Dolls).

https://i.pinimg.com/originals/94/b7/35/94b735bd4afabe91326ed16e1d91e802.jpg

https://popculturereferences.com/wp-content/uploads/2021/10/whos-the-boss-living-dolls-header.jpg

https://i.pinimg.com/originals/d1/4c/91/d14c91877b2e5ee766ad960ed8b817be.jpg

https://www.sitcomsonline.com/photopost/data/701/Who8.jpg

https://static.tvmaze.com/uploads/images/large_landscape/308/771366.jpg

https://www.sitcomsonline.com/photopost/data/701/Who0281.jpg

biffbronson

06-01-2022, 09:14 AM

TMC

06-03-2022, 03:42 AM

TMC

06-06-2022, 05:54 AM

TMC

06-26-2022, 06:42 AM

Some photos that I managed to capture off of CTV.ca from the "Double Dump" (https://i.postimg.cc/pv3WbytG/Who-s-the-Boss-S05-E06-Double-Dump-mkv.jpg) episode. Other than probably the "In Search of Tony" episode at the start of Season 6, this is probably where Alyssa Milano looked her most stunningly beautiful during her time on Who's the Boss?

https://i.ibb.co/zXzC6j4/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-19-04-2022-04-09-02-48-29.jpg

https://i.ibb.co/V06Zqzr/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-18-03-2022-04-09-02-47-38.jpg

https://i.ibb.co/8bCzNKk/Watch-Whos-the-Boss-Season-5-Episode-6-Double-Dump-mp4-snapshot-16-13-2022-04-09-02-55-41.jpg

I think that the hairstyle that Alyssa Milano (https://www.instagram.com/p/CfFXxhJpqT8/) sported during this period (https://64.media.tumblr.com/9a5f8989eaf779523e9585b3934b2364/tumblr_inline_o2pamsR86g1sh134d_640.jpg) was in technical terms, called a "side-sweep" (https://www.google.com/search?q=side+swept+hairstyle+women&tbm=isch&ved=2ahUKEwjsnuiV9sr4AhVHiFMKHfxVDMkQ2-cCegQIABAA&oq=side+swept+hairstyle+women&gs_lcp=CgNpbWcQAzIFCAAQgAQyBggAEB4QCDoECCMQJzoECAAQQ1DPBVjoDmD7EGgAcAB4AIAB-AGIAcgKkgEFMC41LjKYAQCgAQGqAQtnd3Mtd2l6LWltZ8ABAQ&sclient=img&ei=1Ta4YqzgOceQzgL8q7HIDA&bih=757&biw=1600&hl=en) or "side-part" (https://www.google.com/search?q=side+part+hairstyle+alyssa+milano&tbm=isch&ved=2ahUKEwiC3N2y9cr4AhWFwFMKHQ73AI4Q2-cCegQIABAA&oq=side+part+hairstyle+alyssa+milano&gs_lcp=CgNpbWcQAzoECCMQJzoGCAAQHhAHOgYIABAeEAg6BggAEB4QBToFCAAQgARQiQhYoytgvy1oAXAAeACAAdYBiAGGGZIBBjAuMTguMZgBAKABAaoBC2d3cy13aXotaW1nwAEB&sclient=img&ei=Bja4YoLBCYWBzwKO7oPwCA&bih=757&biw=1600#imgrc=2pALLhwkD7nDIM).

https://i.pinimg.com/736x/c5/e2/05/c5e205451a50c64a40dba46af55e18e8--style-movie-s-style.jpg

https://i.ytimg.com/vi/IwOFm0bQAss/maxresdefault.jpg

Tori Spelling during the earlier part of her stint on Beverly Hills, 90210 had that type of hairstyle:
https://pyxis.nymag.com/v1/imgs/84e/a18/9146879a2b0ef89a6acdc038e1bc643844-10-tori-spelling-lead.rsquare.w700.jpg

https://i.dailymail.co.uk/i/pix/2015/05/25/21/2911DCA200000578-3096542-The_beauty_at_work_The_star_in_a_publicity_shot_in_1993_for_Beve-a-2_1432585583631.jpg

TMC

07-14-2022, 12:15 AM

Alyssa guest starring as Samantha Miceli in the pilot episode (https://www.latimes.com/archives/la-xpm-1989-09-26-ca-81-story.html) of Living Dolls (https://twitter.com/dfriend/status/1292217758940311552?lang=tahttp://):
https://pbs.twimg.com/media/Ee7hNC1WAAAz14R?format=jpg&name=360x360

TMC

07-23-2022, 12:04 AM

I think that was the trend to go with those short cuts. It was a way to end the 80's and start fresh in the 1990s.

Given the popularity of Sinead O Connor at the time , her haircut could have been a lot worse :D

https://i.pinimg.com/736x/24/38/f9/2438f958b2a3af40df835e0ece7aa5f8.jpg

I also wonder if Alyssa cut her hair short (https://www.hometheaterforum.com/community/threads/who-was-the-biggest-female-teen-idol-of-the-90s.331909/post-4094415) as a means of getting out of her (https://bestlifeonline.com/most-popular-teen-idol-by-year/) teen idol (https://www.google.com/search?q=teen+idol+alyssa+milano&tbm=isch&ved=2ahUKEwjg1sSDkY75AhUEg2oFHcHxDPMQ2-cCegQIABAA&oq=teen+idol+alyssa+milano&gs_lcp=CgNpbWcQA1DVC1iBE2DXFGgAcAB4AIAB3wWIAdkMkgEJMi0yLjEuNi0xmAEAoAEBqgELZ3dzLXdpei1pbWfAAQE&sclient=img&ei=lXPbYqC4M4SGqtsPweOzmA8&bih=757&biw=1600)/teen heartthrob (https://www.google.com/search?q=teen+heartthrob+alyssa+milano&sxsrf=ALiCzsbntLa7BLVIfPm9t3Io3WfVD7XLeQ:1658549126426&source=lnms&tbm=isch&sa=X&ved=2ahUKEwjpo5f8kI75AhXmkGoFHZkIDKYQ_AUoAXoECAEQAw&biw=1600&bih=757&dpr=1) image (https://www.myjournal.com/celebs/female-teen-idol-year) since her character on the show was entering/in college at that point.

TMC

07-25-2022, 05:33 AM

Thanks everyone for posting all of the great photos. Alyssa looks so glamorous in those above-the-shoulders, curled styles! -- thanks TMC. Really hot. Here are some other curly hairstyles she has rocked:

275819

275820

275821275823

These (https://i.pinimg.com/originals/f8/d9/d1/f8d9d1cc140f3e41179713cb045ff3be.jpg) photos (https://i.pinimg.com/originals/12/99/5d/12995d9ed595de6d8b3b6122f20cfe46.jpg) that I linked are said to be from 1989 (https://www.google.com/search?q=1989+alyssa+milano&tbm=isch&ved=2ahUKEwiX3Izk3ZP5AhUVwikDHSLHCbUQ2-cCegQIABAA&oq=1989+alyssa+milano&gs_lcp=CgNpbWcQAzIGCAAQHhAIOgQIIxAnUNgbWNgbYIofaABwAHgAgAG_AYgB6gKSAQMwLjKYAQCgAQGqAQtnd3Mtd2l6LWltZ8ABAQ&sclient=img&ei=KGPeYpeoCJWEp8kPoo6nqAs&bih=757&biw=1600&hl=en) (circa Season 5).

MikeLutton

07-29-2022, 08:44 PM

just found this one

TMC

07-30-2022, 04:32 AM

i alway's thought sam had nice hair 2 once she got older,

I just remembered that somebody once wrote this (https://web.archive.org/web/20140405003515/http://forums.televisionwithoutpity.com/topic/2874131-whos-the-boss/page-5#entry13039396) on the old TWoP forums:
And I was always soooo jealous of Sam's hair, especially during the fifth and sixth seasons when it was so wonderfully long (https://forums.primetimer.com/topic/112906-whos-the-boss/?do=findComment&comment=6540893).

Also (https://web.archive.org/web/20140406114449/http://forums.televisionwithoutpity.com/topic/2874131-whos-the-boss/page-6#entry13041011)...
I have the whole series on DVDs but I never did end up rewatching the later seasons. Once it got to the short, dark-haired Sam years, the show kind of fell apart, IMO. I also hated the ever diminishing masculinity of Tony, he became a whiny caricature at some point.

TMC

08-13-2022, 03:15 PM

I think that Alyssa looked really pretty here in this interview with Joan Rivers:
E8qBGlonjLw

She kind of looks like her Season 5-early Season 6 self on Who's the Boss? except of course, older.

TMC

09-03-2022, 06:31 AM

Alyssa kind of to me, looks similar to her Season 5-early Season 6 look in this photo from 2015 (https://www.etonline.com/news/171356_alyssa_milano_says_ex_boyfriend_justin_timberlake_and_britney_spears_were_super_love):
https://www.etonline.com/sites/default/files/styles/video_1280x720/public/images/2015-09/1280_ET_INTV_ALYSSA_MILANO_090415.jpg?itok=mECE3xiP

jHvX5kX_BJw

https://www.etonline.com/sites/default/files/styles/video_1920x1080/public/images/2015-09/intv_alyssa_milano_0903_lands.jpg

Alyssa Milano Says 'Divorce Is Not an Option' For Her and David Bugliari (https://www.etonline.com/media/videos/alyssa_milano_says_divorce_is_not_an_option_for_her_and_david_bugliari-171271)

OY-zbswd4-U

E! NEWS - VIVA TOWEL LAUNCH - SEPT 2015 - PART II (https://alyssa-j-milano.com/cpg/thumbnails.php?album=1765)

TMC

09-03-2022, 06:51 AM

TMC

10-07-2022, 10:20 PM

First of all I couldn't agree with you more on everything you said - and that picture of her in Jamaica is how my brain references her at all times. Like even today I like to imagine her that way, because I remember she was seriously the hottest thing that every guy I knew had ever seen at the time.

Also I remember the writers seemed to go out of their way to have Tony reference her darker hair ("you didn't clear that with me" or something to that effect). So I wonder if it's something Milano wanted, like she didn't want to be the sexy girl with long hair anymore. I recall Becky from Roseanne wanted a shorter hair cut but the producers said "no you're from a small town and you're poor, you should have normal long blond hair". So Roseanne grabbed a pair of scissors and cut out a chunk of her hair, forcing them to give her one of those early 90s bob cuts.

Boy George went through a similar thing in the mid 80s when he said he began to feel like a doll, so he cut off his hair with that "chopped up" black hair cut that was featured in their 1986 album cover.

But at the same time it would be totally possible that the network was like "ok she's being too sexy, lets make her more wholesome"... but I can't imagine they'd do that when their market research would've shown she has reached iconic status among teen boys (Italian or otherwise!)

I saw that episode again today, and I'm beginning to wonder if that was an inside joke. I would assume that it's typically frowned upon for actors (especially women) to drastically alter their hairstyle when production for a television season is on-going. This is because it really wrecks havoc with the continuity. Alyssa Milano's future Charmed co-star, Shannen Doherty was fired from Beverly Hills, 90210 in part but not just because she cut her hair in the middle of the season.

And with Who's the Boss?, Alyssa first sports her darker hair style in the eighth episode of Season 6, "Supermom Burnout" (https://www.youtube.com/watch?v=jj5xQND1AEk) and yet in the 12th episode of that year, "Gambling Jag", Alyssa's hairstyle is back to the way that it was at the very start of the season. So of course, ABC originally broadcast the two episodes out of order.

TMC

07-09-2023, 04:32 AM

Some images from the "In Your Dreams" episode from Season 6.

Alyssa Milano's Fourth of July 2023 photos (https://www.instagram.com/p/Cudn3l0roHs/) reminded me of the way that her hair looked in the "In Your Dreams" episode.

TMC

09-05-2023, 01:21 AM