He’s got several that are quite dark (and funny as hell) in various ways.
Nine Inch Nails’ “Big Man With a Gun” is an example of the singer creating a monsterous character. Literally “dick-ish”. As far as I know, Trent Reznor is not that way. I’ll let you Google the song & lyrics yourself.
Pearl Jam’s “Glorified G” is another example. This time, the gun is just a metaphor for a gun, not a penis (er, well kind of it is, but not the same as the other song)
“Got a gun, fact I got two
That’s OK man, 'cause I love God
Glorified version of a pellet gun
Feels so manly, when armed”
Stevie Wonder’s “Part-Time Lover” is “how to” advice.
Call up, ring once, hang up the phone
To let me know you made it home
Don’t want nothing to be wrong with part-time lover
If she’s with me i’ll blink the lights
To let you know tonight’s the night
For me and you my part-time lover
…
If i’m with friends and we should meet
Just pass me by, don’t even speak
Know the word’s “discreet” when part-time lovers
Of course, at the end he finds out that his wife also has a part-time lover.
I’m probably being much too harsh, but Joan Baez’s “Please Come to Boston” has always annoyed me - her lover is always on the road and begging her to join him, but she says:
“hey ramblin’ boy now wontcha settle down?
Boston ain’t your kinda town
There ain’t no gold and there ain’t nobody like me
I’m the number one fan of the man from Tennessee”
So, basically, instead of being willing to share in his adventures and experience new things with him, she’s saying he should give it all up and come home to her because she’s superior to anything he’s going to find in the wider world. That seems both controlling and egotistical to me. If they’re that different, and she’s a homebody and he’s got itchy feet, maybe she should let him go find someone better suited to his rambling ways while she stays home and marries the boy next door who doesn’t want to travel either.
I was tired of my lady
We’d been together too long
Like a worn out recording
Of a favorite song
I think you all know this song.
https://www.google.com/search?client=firefox-b-1-e&q=pina+colada+song+lyrics
Allman Brother’s Ramblin’ Man is another example of ‘Hey, babe, this is just who I am.’
Ricky Nelson’s Traveling Man is a serial philanderer.
I Know What Boys Like by The Waitresses. Bitchitude?
I make them want me
I like to tease them
They want to touch me
I never let them
Dion’s “The Wanderer” maybe is the most extreme song of that type. It’s a brag from start to finish how he travels around and breaking hearts of girls left and right without even telling them his name:
ETA: this reminded me of another blatantly misogynistic early rock’n’roll song, Eddie Cochran’s “My Way” (could have been one of John Lennon’s favorite songs. The Who covered it):
Yes - that’s it. I’m being tongue-in-cheek, I’m sure Pete Burns is a lovely person - or at the very least, I simply don’t know. I think it’s the hallmark of a great lyricist to inhabit different personas. Sting, for instance, has been a lovesick john, perv teacher, stalker, murderer, and a divorced dad with custody of his kids on the weekends. None of those personas really match up with him as person, AFAIK.
I recently saw something where someone was suggesting that Sting was problematic because of “Don’t Stand So Close To Me,” particularly because he was a teacher for some time. 
CairoCarol, I agree with you 100% about “Please Come To Boston”, that song has always annoyed me for the exact same reason you said. What a clingy, controlling wet blanket the singer sounds like!
The same could hold true for all singers mentioned in this thread. I don’t believe Johnny Cash shot a man in Reno just to watch him die, but it seems a fair amount of posters in this thread think Sting and John Lennon are authentic and not portraying characters.
In general I totally agree that singers often impersonate a character that’s not their own in songs, but the thing with Lennon is that it has been reported a lot of times that in real life he really was the controlling, hyper-jealous jerk of songs like “Run For Your Life”, “Jealous Guy” and “You Can’t Do That”.
Baez did cover the song later, but the only version I know is the original by Dave Loggins, which was a top-ten hit in 1974.
A cursory glance proves that Patti D’Arbanville inspired Cat Stevens’ Wild World.
Dodged a bullet there, she did.
Although I liked the Beatles tune “Norwegian Wood”, I have a new perspective ever since someone on these boards pointed out that it can be interpreted that at the end the singer sets fire to the “girl’s” furniture or room.
I once had a girl
Or should I say she once had me
She showed me her room
Isn’t it good Norwegian wood?
.
.
.
And when I awoke I was alone
This bird had flown
So I lit a fire
Isn’t it good Norwegian wood?
I’m surprised nobody’s mentioned The Mamas & the Papas’ “I Saw Her Again,” written by Denny Doherty (and John Phillips) about Doherty’s brief fling with Phillips’ wife, Michelle:
I saw her again last night
And you know that I shouldn’t
To string her along’s just not right
If I couldn’t I wouldn’t
But what can I do, I’m lonely too
And it makes me feel so good to know
You’ll never leave me
So yeah, you’re stringing her along because you’re lonely and it’s so gratifying to know she won’t leave you. Ugh.
Heart’s “All I want to do is make love to you” has the woman showing the dickitude.
Her man is shooting blanks so she goes out, hooks up with a stranger, uses him to get pregnant, then ghosts him.
And in the mornin’ when he woke
All I left him was a note
I told him I am the flower, you are the seed
We walked in the garden, we planted a tree
Don’t try to find me, please don’t you dare
Just live in my memory, you’ll always be there
Then it happened one day
We came 'round the same way
You can imagine his surprise
When he saw his own eyes
I said, “Please, please understand
I’m in love with another man
And what he couldn’t give me, oh-oh
Was the one little thing that you can”
There’s another interpretation that’s more benign.
I’m inclined to believe that interpretation. Lennon was an asshole, but not that much of one.
Jimmy Dean (not to be confused with James Dean) had a few winners back in his day.
Little Black Book (1962) – kinda funny but still a bit jerkish. To be fair, he described all his girlfriends as being jerkish too.
But his real winner was his hillbilly hick song I Won’t Go Hunting With You Jake But I’ll Go Chasing Wimmen (1961) which, IIRC, was on the flip side of Big Bad John.
Huh, I had always interpreted that final line as saying “and you were just a prop, too” rather than “this isn’t the first time I’ve cheated on you.” But you’re right, it could be either one. I’m not sure which is more dickish.
Yup, the epitome of clueless dickitude.