Thank you, suranyi. Another example to use in my “Was Dave Marsh ever right about anything?” rant.
Not sure if this is cheating because the song is so short, but “Dig it” by The Beatles might qualify.
This is one of those songs which is difficult to quote from without including all the lyrics, but here goes:
Like a rolling stone
Ah, like a rolling stone
Like the FBI and the CIA
And the BBC–BB King
And Doris Day
Matt Busby
Steve Malkmus and Pavement made a career out of doing this subtly, sometimes not so. Steve Malkmus took great pride in throwing in guitar licks that would quote other songs in an ironic fashion.
“Now what about the voice of Geddy Lee?
How did it get so high?
I wonder if he talks like an ordinary guy?
I know him and he does…
Well you’re my fact checkin’ cuz”
–Stereo by Pavement
I would also nominate the now thankfully forgotten song “Sister” by the Juliana Hatfiled Three, out of the big Boston pop scene of the early 1990s.
But my favorite is by Zappa, the on the album “Mothers Live at the Fillmore East 1971.” The Mothers at that time were ex-members of the band The Turtles, who had a big hit in the 1960s with “Happy Together.” The album ostensibly focuses on an incident famous in rock history, involving The Vanilla Fudge, groupies, a primitive video camera, a motel on a Seattle pier called the Edgewater Inn, and a mudshark caught by one of the band members (or maybe IIRC John Bonham) from the motel room, from which you could fish from the window. The Mothers play both the band and the groupies following them. The groupies want to do it with a band who has a hit record in the charts (with a bullet). The band want the groupies to “come in my bus.” The groupies agree, but want to hear the hit record. So the Mothers oblige, and break into “Happy Together.” It is a bizarre, twisted, half hour of music, ending in one of the sweetest, most innocent songs ever recorded.
At post 53 ‘Good News Week’ was mentioned. I disagree that it fits the criteria- it tends to comment on (then) social issues - I think it was about 1963- but from my now limited memory I didn’t think it was reflecting pop culture.
I offer one- Randy Scouse Git (Alternate Title) by the Monkees. Lyric ‘The four kings of EMI are sitting stately on the floor’ was a reference to the Beatles. So it’s not a onstant reference 
I haven’t thought of this in years, but “West End Avenue” from Stephen Schwartz’s “The Magic Show” fits in here.
Kate Bush does the dead pop/rock star thing in “Blow Away” (from the album Never For Ever, 1980), envisioning a jam session in the afterworld (“Bolan and Moony are heading the show tonight”) featuring Marc Bolan, Minnie Riperton, Keith Moon, Sid Vicious, Buddy Holly, and Sandy Denny.
However, there’s more to the song than a list of dead musicians. 
A Simple Desultory Philippic (Or How I Was Robert McNamara’d Into Submission). My favorite song title ever.
Did anyone mention the Theme to *Rocky Horror Picture Show * yet?
Which brings to mind Forbidden Broadway’s “Let’s Ruin Times Square Again.”
There’s a Gap on the left and HMV on the right.
Buy a ticket to Rent, where they push drugs all night.
And for the midtown sleezy, we’ve got a very bad yen-en-en-en-en-en
Let’s ruin Times Square again.
That’s odd, considering that the IRT (aka the numbered subway lines in NYC) doesn’t stop at 4 St.