I'll start with my faves first:
1.
Janet Jackson - "If" and "Pleasure Principle" are Janet's two most overrated songs and videos. The
janet. album really isn't
THAT much better than
All For You.
Discipline is better than both
Damita Jo and
20 YO. RN1814 is better than TVR, and
Control is better than
janet.. Janet > Michael.
2.
Stevie Wonder - some of his 70s works sounds like elaborate recreations of his 60s work. The "Characters" album flat out sucks aside from like 3 tracks. He is arguably the most talented solo artist ever, however.
The "Fullfillingness" album leaves a lot to be desired, esp being sandwiched between Innervisions and Songs... .
3.
Christina Aguilera - I think she makes a lot of music that will appreciated somewhere down the road. She needs a career make over and intensive vocal training. That Rolling Stone list and "Voice of Our Generation" title has really gone to her head. She acts as if her music is the pinnacle of greatness, when in reality it's just un-cohesive hogwash. She struggles to put together a cohesive album with flow. Back To Basics > Stripped, btw.
And just randoms:
4.
Michael Jackson - probably the most overrated artist of the past 30 years. He was only good for Off The Wall, Thriller, and Bad. The rest of his catalog is pretty forgettable. If he hadn't spent the last 20 years of his career copying Janet, he probably would be good for more than those aforementioned three albums.
5.
Whitney & Mariah - two great singers with discographies that leave a lot to be desired. Mariah seems to be too concerned with commercialness and being "eternally 12", rather than showing some artistic integrity. I think that's why none of her albums are highly regarded by the critics. Whitney, well, Clive, just wouldn't let her write her material. Some of her unreleased stuff is better than what's on the album.
6.
Usher - is probably the most successful artist of the past decade, but easily the most forgettable. He hasn't had a single memorable performance, and I wouldn't even consider him an icon. He's talented, and the best male entertainer behind MJ, James, and Prince, and the best male dancer after MJ. He has so much potential, but his albums are a snore for the most part.
8.
Beyonce - Overrated, musically. For someone of her talent, you would think her albums would be groundbreaking and transcendent, but they're not. I haven't read any articles or seen the influence her albums have had on the industry or other artists. She doesn't have an album that is widely acclaimed, or a legendary album. How she has 16 Grammys is a result of her lack of competition in her respective field.
9.
Rihanna - None of her music has a chance at being classic.
10.
Britney Spears - In The Zone > Blackout. Out of all of her peers, she's the least talented.
11.
Lady Gaga - Her next album will determine how long she'll be around. After people get tired of her shtick, she can nip it in the bud. She needs to change up her style if she wants to be around long.
12.
Today's artists - the pool of artists of the last 15 years will never be great as their predecessors. They appear to lack the overall talent and drive of the artists from the 60s, 70s, and 80s (+Mariah). They haven't produced any legendary albums that have signaled a change in music, no "moments" in pop culture, and are just overall lacking in every necessary department. No artists will be seen as legends in the same light as the artists who came before them.
.
But yet again, probably just me.
Yes, prove him wrong by example. 
