if I'm not mistaken, there have been 19 successful MITB cash-ins. so, here's my ranking of each one + personal thoughts on each one.
19. Brock Lesnar cashes in on Seth Rollins [Extreme Rules 2019]
thoughts: he shouldn't have even won the briefcase, let alone cash in successfully.
thoughts: he shouldn't have even won the briefcase, let alone cash in successfully.
18. Jack Swagger cashes in on Chris Jericho [Smackdown: April 2, 2010]
thoughts: don't care.
thoughts: don't care.
17. Rob Van Dam wins his pre-announced cash-in match against John Cena [One Night Stand 2006]
thoughts: never cared about RVD, nor did I care about this title win.
thoughts: never cared about RVD, nor did I care about this title win.
16. Kane cashes in on Rey Mysterio [Money in the Bank 2010]
thoughts: rey mysterio robbed yet again.
thoughts: rey mysterio robbed yet again.
15. Alberto Del Rio cashes in on CM Punk [Summerslam 2011]
thoughts: i might have ranked this higher, had the cash-in not come at the expense of punk
thoughts: i might have ranked this higher, had the cash-in not come at the expense of punk
14. Daniel Bryan cashes in on Big Show [TLC 2011]
thoughts: from now on are all the cash-ins that i loved. this one was so out of the blue tbh but it was great. michael cole sold this wonderfully lmao
thoughts: from now on are all the cash-ins that i loved. this one was so out of the blue tbh but it was great. michael cole sold this wonderfully lmao
13. Edge cashes in on The Undertaker [Smackdown: May 8th, 2007]
thoughts: loved it, dunno what else to say tbh.
thoughts: loved it, dunno what else to say tbh.
12. Edge cashes in on John Cena [New Year's Revolution 2006]
thoughts: very first cash-in so i put it above his second cash-in. i pretty much share the same thoughts tho.
thoughts: very first cash-in so i put it above his second cash-in. i pretty much share the same thoughts tho.
11. Bayley cashes in on Charlotte [Money in the Bank 2019]
thoughts: never was a fan of bayley (until her current heel run which i really love), but i couldn't help but smile and feel happy for her.
thoughts: never was a fan of bayley (until her current heel run which i really love), but i couldn't help but smile and feel happy for her.
10. Alexa Bliss cashes in on Nia Jax [Money in the Bank 2018]
thoughts: we all knew she was just a transitional champ for Ronda but still, PRETTY ICONIC i'd say
thoughts: we all knew she was just a transitional champ for Ronda but still, PRETTY ICONIC i'd say
9. CM Punk cashes in on Jeff Hardy [Extreme Rules 2009]
thoughts: absolutely amazing, and the fact jeff actually kicked out of the gts made this even more iconic
thoughts: absolutely amazing, and the fact jeff actually kicked out of the gts made this even more iconic
8. Sheamus cashes in on Roman Reigns [Survivor Series 2015]
thoughts: i really don't know why i like this so much, but i just do.
thoughts: i really don't know why i like this so much, but i just do.
7. Randy Orton cashes in on Daniel Bryan [Summerslam 2013]
thoughts: truly one of the most iconic cash-ins.
thoughts: truly one of the most iconic cash-ins.
6. CM Punk cashes in on Edge [RAW: June 30th, 2008]
thoughts: i always get chills
WHAT A MOMENT!!!!
thoughts: i always get chills

5. Carmella cashes in on Charlotte [Smackdown: April 10th, 2018]
thoughts: the kick didn't connect, but this was a great cash-in to cap off an entertaining run with the briefcase!
thoughts: the kick didn't connect, but this was a great cash-in to cap off an entertaining run with the briefcase!
4. The Miz cashes in on Randy Orton [RAW: November 22, 2010]
thoughts: IMO the most underrated cash-in. one of my favs certainly
thoughts: IMO the most underrated cash-in. one of my favs certainly
3. Dean Ambrose cashes in on Seth Rollins [Money in the Bank 2016]
thoughts: do I even need to say anything about this iconic night?
thoughts: do I even need to say anything about this iconic night?
2. Seth Rollins cashes in on Brock Lesnar & Roman Reigns [WrestleMania 31]
thoughts: the video speaks for itself.
thoughts: the video speaks for itself.
1. Dolph Ziggler cashes in on Alberto del Cunt [RAW: April 8th, 2013]
thoughts: sad his reign was cut short but the pop he got and the victory was....whew.
thoughts: sad his reign was cut short but the pop he got and the victory was....whew.