History Series / ILoveMoney

* JerkassHasAPoint: As hostile as Buckwild and Saaphryi were in this season, they were right about how Leilene was focusing too much on finding love in a competition setting. They were also right about how Buddha was just trying to manipulate Leilene.

** 20 Pack was put into a situation where - regardless of who he sent home - he was still sending an ally of his away, thereby diminishing his alliance's chances of making it all the way to the end. [[spoiler: He emphasized he did not want to void Buckwild's check, because he did not want to separate her and Saaphyri, but also did not want to just void Frenchie's check because of how helpful she had been to him. When told to void Buckwild's check because everyone got tired of her antics, 20 Pack complied. Saaphyri quickly turned on him for that, without recognizing the hell he was going through during the elimination procedure.]]

* FailureIsTheOnlyOption: Frank appears to be framed as having this trope afflicted upon him. From the very beginning of Season 1, The Entertainer was seen as "a loser" for his eccentric mannerisms and for still living in his parents' basement. This at least gave him a clear motive to have the $250,000 cash prize, as he wanted to cut ties with his parents and improve his life. This winds up giving him an "underdog" persona in ''I Love Money 1,'' as most of the other contestants rapidly grew tired of his shenanigans. He still endeared himself to Destiney, Heather, and 12 Pack, all of whom he allied with and tried to help however he could. When Frank recognizes he erred in sending Heather home instead of Megan during elimination, he tries to make the best of his mistake by being more competitive. His aspirations are dashed due to the Pole Riders In The Sky challenge, which was one he could not have hoped to prepare for. He realizes he's screwed; rather than allow any of the remaining contestants to void his check, he deliberately chooses to be the Dead Last Loser, which is played for tragedy.

* UnlimitedWardrobe: During ''I Love Money 2,'' Myammee lost a suitcase, and only really had her lingerie and the clothes she came in.

* ChronicBackstabbingDisorder: There was a challenge in ''I Love Money 1'' which involved throwing daggers behind the backs of mannequins created of the contestants who made it far enough to participate in said challenge. As a result, this trope was parodied.

For a chance to win $250,000,- and a couple of extra hours on TV, the contestants must win a series of challenges, hosted by [=VH1=] personality Craig J. Jackson. Much of the show's appeal lies in watching Jackson slowly realize he's taken a wrong turn in his career path: he visibly goes from generic TV host enthusiasm to boredom, then to abject horror, and finally (around season 2) to simply enjoying the show for what it is. By the time the season 2 finale came around, he was really getting in on all the fun.

* OnlySaneMan: 20 Pack. He breaks his hand during the second game, and instead of making a big drama out of it, he just continues to be a solid part of his team. He was voted "most trustworthy" by ''everyone'' except Frank (who voted for himself).
** And once again, just like in ''Series/FlavorOfLove'', Hoopz is the [[OnlySaneMan Only Sane Woman]]. And [[spoiler: wins the show.]]

* ChronicBackstabbingDisorder: There was a challenge in ''I Love Money 1'' which involved throwing daggers behind the backs of mannequins made of the contestants who made it far enough to participate in said challenge. As a result, this trope was parodied.

* ChronicBackstabbingDisorder: There was a challenge in ''I Love Money 1'' which involved throwing daggers behind the backs of mannequins made of the contestants who made it far enough to participate in said challenge. As a result, {{Creator/VH1}} implied it was directly invoking and mocking this trope.

** In Season 2, Heat's elimination was remembered by the Entertainer to the point where "the same freakin' waiter" was also present. In addition, the Entertainer's downfall was a challenge hovering above water, [[spoiler: just like in Season 1]].
** Tamara's presence on the first episode of Season 2 wasn't too different from her presence on Rock of Love, being not only short, but involving her getting directionally confused as to how to get out of the mansion in ILM. This is precisely the same thing that happened once she was eliminated on ROL.

* RevengeBeforeReason: It's implied to have caused a majority of the ensuing problems in ''I Love Money 2.''

* FailureIsTheOnlyOption: Frank appears to be framed as having this trope afflicted upon him. From the very beginning of Season 1, The Entertainer was seen as "a loser" for his eccentric mannerisms and for still living in his parents' basement. This at least gave him a clear motive to have the $250,000 cash prize, as he wanted to cut ties with his parents and improve his life. This winds up giving him an "underdog" persona in ''I Love Money 1,'' as most of the other contestants rapidly grew tired of his shenanigans. He still endeared himself to Destiney, Heather, and 12 Pack, all of whom he allied with and tried to help however he could. [[spoiler: When Frank recognizes he fucked up in sending Heather home instead of Megan during elimination, he tries to make the best of his mistake by being more competitive. His aspirations are dashed due to the Pole Riders In The Sky challenge, which was one he could not have hoped to prepare for. He realizes he's screwed; rather than allow any of the remaining contestants to void his check, he deliberately chooses to be the Dead Last Loser, which is played for tragedy.]]

* HeelRealization: In Season 1, after [[spoiler: having eliminated Heather, The Entertainer quickly recognizes his mistake and tries to redeem himself in her eyes, by trying to win the next challenge. Likewise, he promises to get revenge on Megan for having manipulated him into voiding Heather's check. Unfortunately for him, the next challenge - Pole Riders In The Sky - was one he was in no way prepared for (even by his own admission). Because he was not equipped to handle Pole Riders In The Sky, he began contemplating things and recognized he was not going to last much longer after this challenge. He deliberately fell in the water, conceding he was "going back home" to his {{Jerkass}} parents and accepting his role as Dead Last Loser of the challenge. As a consequence, his check winds up getting voided outright by CJ. He surprisingly takes it in stride, though part of his graceful defeat is in recognizing how much he screwed up to begin with.]]

* ManipulativeBitch: Megan.

** Upon sensing foul play from 20 Pack and T-weed, [[spoiler: Tamara]] almost considers rage-quitting in the first Episode. [[spoiler: She is talked out of it, with people having been made assured Buddha would be going home. T-weed's double-cross winds up causing her to go home instead.]]

*** Heat, Destiney, and The Entertainer. The Entertainer had feelings for her, but Destiney and Heat were dating at the start of ''I Love Money 1.'' [[spoiler: Destiney eventually breaks up with Heat, and The Entertainer swoops in. As a result of the breakup and as a result of 12 Pack and Heat distancing themselves from each other, The Entertainer is allowed to eliminate Heat, with minimal consequence.]] To add insult to injury, [[spoiler: alliance-related melodrama causes Destiney to have her check be voided not long after, making the romance between her and The Entertainer short-lived anyway.]]

** Buddha in Season 2 was a zig-zagged case of this. While his being a prime elimination target was also the result of a long-standing feud between himself and The Entertainer from their ''I Love New York 2'' days, Buddha was immensely antisocial and mean-spirited towards the other contestants. His malice ended up causing 20 Pack and T-weed to make a deal to not include him on either team. [[spoiler: While 20 Pack kept his word, T-weed didn't.]]

* OffTheRails: ''I Love Money 2'' was supposed to have [[spoiler: Buddha]] be the first contestant eliminated, because [[spoiler: his strength as a contestant and his generally unpleasant behaviour were both highly frowned upon.]] However, [[spoiler: T-weed recruits him anyway in an act of sheer arrogance.]] Not only does the plan get derailed, but it takes roughly four people's checks being voided (including the check of the person who actively went against the plan for their own selfish ends) ''and'' [=VH1=] intervening to normalize the game state as a result of these plans being derailed.

** A plan to get Buddha out of the house was cooked up by members of the Green Team, where [[spoiler: Leilene]] would quit so someone else would get their check voided by the Paymaster. Theoretically, the plan was concocted with Buddha being presumably up next after the departure. However, [[spoiler: Leilene winds up not going through with the plan, muc to her friends' frustration, because she was talked out of it by the aforementioned Paymaster (who happened to be Heat).]]

** A large majority of ''I Love Money 2'' can be explained by Tailor Made, Buddha, and The Entertainer all being unable to reconcile their differences from ''I Love New York 2,'' and everyone else in the cast getting caught up in their long-standing feuds. While Tailor Made wanted to let go of his grudges, the other two absolutely did not.

** A large majority of ''I Love Money 2'' is an example of Tailor Made, Buddha, and The Entertainer all being unable to reconcile their differences from ''I Love New York 2,'' and everyone else in the cast getting caught up in their long-standing feuds. While Tailor Made wanted to let go of his grudges, the other two absolutely did not.

** A plan to get [[spoiler: Buddha]] out of the house was cooked up by members of the Green Team, where [[spoiler: Leilene]] would quit so someone else would get their check voided by the Paymaster. Theoretically, the plan was concocted with [[spoiler: Buddha]] being eliminated after the departure. However, [[spoiler: Leilene winds up not going through with the plan, much to her friends' frustration, because she was talked out of it by the aforementioned Paymaster (who happened to be Heat).]]

*** [[spoiler: Buddha's persistent presence, despite everyone wanting him gone, was such where [=VH1=] had to step in and intervene. [=VH1=] gave everyone a chance to send Buddha home, and both 20 Pack and Saaphyri gladly took it.]]

* HesBack: This is personally invoked by [[spoiler: Frank the Entertainer in Season 2, as he did not take his loss in Season 1 lightly. He's also implied to have taken [[TookALevelInBadass a level in badass]] in the interim between ''I Love Money 1'' and ''I Love Money 2,'' though his increased ruthlessness in the latter is noticed to such a degree it borders on TookALevelInJerkass and is also responsible for his downfall in the second season.]]
** [[spoiler: Heat also tries to invoke this in ''I Love Money 2.'' He lasts long enough to be pivotal to the victory of a few challenges, but he is still eliminated early and in much the same situation as in ''I Love Money 1.'']]
** Downplayed in Season 4[[spoiler: with 20 Pack. He only lasts two Episodes.]]

* OffTheRails: ''I Love Money 2'' was supposed to have [[spoiler: Buddha]] be the first contestant eliminated, because [[spoiler: his strength as a contestant and his generally unpleasant behaviour were both highly frowned upon.]] However, [[spoiler: T-weed recruits him anyway in an act of sheer arrogance.]] Not only does the plan get derailed, but it takes roughly four people's checks being voided ''and'' [=VH1=] intervening to normalize the game state as a result of the plans being derailed so fast.

* TheMole: Milf and Onix both fail spectacularly at being this.
* ObfuscatingStupidity: Megan's main tactic.
** Discussed with It in the second season finale (Even the promos promoted the idea). But It proves to be just ''that'' stupid. [[spoiler:He doesn't even complete the final challenge.]]
* OddFriendship: Tailor Made and It.