I don't necessarily agree with the idea that Hail to Reason/Buckpasser doesn't work. Buckpasser over Hail to Reason (or vice versa) has worked a few times. Witness the hardy Silver Buck, a grade I winner by Buckpasser out of a Hail to Reason mare. I will admit, though, that Silver Buck's dam, Silver True, was a rather tough mare, as she ran 38 times. Another of her foals ran 79 times. One of Hail to Reason's sons, Stop the Music, was a good stakes winner and sire, but was not out of a Buckpasser mare (he was out of a mare by Buckpasser's sire, Tom Fool).
Interestingly enough, though, more distant descendants of both horses seem to cross well.
http://www.stallions.com.au/newsv2/sp_Star_Cross.asp
Southern Halo has done very well with mares by Logical, a son of Buckpasser.
The sire of more than 550 winners and more than 130 stakes winners - one of the few sires to top 100SW - Southern Halo has sired quite a few of his 47 Gr.1 winners out of mares by Logical (a son of Buckpasser), who is the sire of Other Star, dam of Star Cross.
Some of the Gr.1 winners bred on this cross are Gouache, Venusberg, Hangar (Argentine Derby), Matthis and his Tasmanian-based brother My Lad (ARG), Rimel, La Costa Azul, La Galerie (Champion 2YO) and Wally (Champion Sprinter).
Halo, a son of Hail to Reason, crossed with Buckpasser's stellar daughter Sex Appeal to produce the mare Solar. Solar was a multiple group III winner and the ancestress of graded stakes winner Strong Hope and group I winner Bahamian Pirate.
Roberto also had a group-placed horse out of a Buckpasser mare in Al Mufti, who went on to be a leading South American sire.