To give you a better idea (https://www.reddit.com/r/ToddintheShadow/comments/w4uvw4/is_pool_it_by_the_monkees_a_trainwreckord/):

With Summer In Paradise (https://tvtropes.org/pmwiki/pmwiki.php/Music/SummerInParadise) and American Dream, failed modernized comeback albums from boomer era bands is starting to become something of a running theme on Trainwreckords (https://tvtropes.org/pmwiki/pmwiki.php/WMG/ToddInTheShadowsTrainwreckords), so I'd like to submit another example. In the mid to late 1980's, The Monkees had managed to forage something of a comeback (https://tvtropes.org/pmwiki/pmwiki.php/CareerResurrection/Music) in the world of popular culture, with reruns of their TV show on MTV and Nickelodeon being a huge hit, and 1986 yielding the band their first top 20 hit in 18 years with "That Was Then, This Is Now" (https://en.wikipedia.org/wiki/That_Was_Then,_This_Is_Now_(song)). But any chances of furthering that comeback were completely shot in the foot with this album (https://en.wikipedia.org/wiki/Pool_It!) (their first in 13 years), with its awful album cover (another running theme on Trainwreckords) likely alienating many potential listeners, and The Monkees bizarre attempts at tackling genres outside their usual wheelhouse (they try doing a reggae type song at one point) drawing away those who were left.

In case you don't know, there's this internet music critic named Todd in the Shadows (https://www.youtube.com/c/ToddintheShadows). A recurring segment of his is called "Trainwreckords" (https://thatguywiththeglasses.fandom.com/wiki/Trainwreckords), which examines supposed career killing (https://tvtropes.org/pmwiki/pmwiki.php/CreatorKiller/Music) albums of once hugely successful artists.

THE ALBUMS THAT RUINED US: “Pool It!” by The Monkees (https://rougeazul.wordpress.com/2023/04/01/the-albums-that-ruined-us-pool-it-by-the-monkees/)

Pool It! is,was and always will be a disaster. The Monkees had a habit of trying to sound "modern" with both Pool It! and Justus. It just wasn't what they were good at, and also not what the fams wanted. They finally got it right with Good Times! Pool It! was just an over-synsthized mess, along with some poor song choices (see She's Movin' In With Rico).

What comeback?

MTV started running the old show, the group got to number 20 with That Was Then, This Now and that was pretty much it. Kind of reminded me of The Mills Brothers who had a hit in 1968 (Cab Driver) which peaked at 23.

The guys were all over 40, they weren't going to become hitmakers again, I don't think Pool It ruined their comeback, they were destined at that point in there careers to be a nostalgia act.

What comeback?

MTV started running the old show, the group got to number 20 with That Was Then, This Is Now and that was pretty much it. Kind of reminded me of The Mills Brothers who had a hit in 1968 (Cab Driver) which peaked at 23.

The guys were all over 40, they weren't going to become hitmakers again, I don't think Pool It ruined their comeback, they were destined at that point in their careers to be a nostalgia act.