Ultimate Monk (DnD Optimized Character Build)/Multiclassing the Ultimate Monk
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Plunging into the class progression tables for the first time, certain variants may give the appearance of a crowded jumble of classes placed atop each other with no rhyme or reason. Each class and each level, however, serves a critical purpose in maximizing the effectiveness of the Ultimate Monk (both from a raw-power perspective and a roleplaying (providing abilities and tactical options that are dramatic and fun to use) perspective. The classes used in the 3.5E progressions, and the reasoning behind them, are listed below.
That an Ultimate Monk needs levels in monk should come as a surprise to no one, but what is character optimization, if not a process by which we question what we think we know about the limits of a player's choices? But in this case, we do need the monk; no one else has the monk's unarmed strikes, fast move, and flurry abilities (not to mention he is the prerequisite class for another essential class, Psionic Fist.)
A harder question is, how many level of monk do we need? You can get by with as few as 3, which opens the door to Psionic Fist. A Monk 3/Psionic Fist 12 with a Monk's Belt has maximal damage from unarmed strikes (which is a mark the Ultimate Monk always must hit.) On the other hand, many good things await the monk on the standard progression. If he abandons it at Monk 3, he will never achieve ki Strike (magic) (4th), removal of the flurry attack penalties (at 5th and 9th levels), a bonus unarmed combat feat (6th), improved evasion (9th), greater flurry (11th), immunity to poisons (11th), dimension door (12th), SR (13th), or ki strike (adamantine) (16th). (There are many other abilities you lose out on, of course, from slow fall to the potentially lethal quivering palm attack (15th); but in the author's opinion, it is the (lack of the) powers listed above that really hurt.)
There is no settled answer to how many levels of monk one needs, but the Ultimate Monk will in most variations take at least 11 levels. The primary drivers of that decision are the combat feat, improved evasion, and greater flurry. Ki strike (adamantine) is mostly a cinematic flourish for the monk, whose massive-damage strikes laugh at hardness deductions anyway. There are other ways to get spell resistance; there are other ways to access dimension door.
The Psionic Fist prestige class allows you to continue to improve the monk's AC, unarmed damage, and move bonus whilst rapidly acquiring devestating combat buffs via the Psychic Warrior power list: Claws of the Beast, Precognition, Offensive, Inertial Armor, Animal Affinity, Psionic Lion's Charge, Empathic Transfer, and finally, via the Expanded Knowledge feat, Metamorphosis. Metamorphosis is at the heart of the build and every variant must have at least 9 levels of Psionic Fist, to access it. Usually we will prefer 10 levels, for the extra 5th-level power and for the increase in the Ultimate Monk's power point reserve. Some variants may go higher, to increase the effective manifester level of the monk's powers (most of them scale, meaning every increase in manifester level increases the combat power of the monk considerably). Also note that the combined monk + psionic fist level continues to bring AC and speed bonuses after level 20, as shown on the Epic Monk table.
 Drunken Master
The primary attraction of the drunken master prestige class (introduced in Complete Warrior) is Stagger, an ability acquired at the second level which allows the monk to move in any pattern (not just in a straight line towards the foe) in a charge action. This is more flexible than the single 90 degree turn offered by some other feats (Psionic Charge, Fleet of Foot) and is extremely powerful, especially when combined with abilities (like Psionic Lion's Charge) that allow the monk to make a full attack after charging, and/or the Hustle power, which allows an extra move action, which can allow the monk to move after charging.
The ability to do unarmed strike damage with improvised weapons is also highly useful at the upper levels, when the monk's unarmed strike abilities far outstrip normal weapon damage (and improvised weapons, unlike bare hands, can also be thrown.) Two levels of Drunken Master are optimal.
Ultimate Monks take one or two levels of Psychic Warrior in some variants, mostly for the bonus feats. These can be psionic feats or fighter bonus feats. If the acquisition of psychic warrior levels is delayed to after the 20th level, they may be Epic feats.
Psychic Warrior also gives the player a couple more first-level powers, and a slightly increased power reserve. It does not change the monk's manifester level, however; levels in psychic warrior overlap with, and do not stack with, levels in psionic fist.
On no account should the Ultimate Monk take more than two levels in psychic warrior.
Ultimate Monks take one or two levels of fighter for the same reason they take psychic warrior: feats. The same considerations apply.
A single level of elocater gives the Scorn the Earth ability, which allows the monk to run or charge over any sort of terrain, move across leaves through treetops or along the edge of a sword. The impact of this power is partly cinematic, but mostly practical. Especially combined with the two levels in drunken master, it gives a character who can charge in most situations. And the usefulness of the extremely high base move of the monk is greatly potentiated by an ability that removes restrictions on movement and, indeed, opens up new vistas.
The first-level elocater gains +1 manifester level in an existing class, so it is important to pick up elocater only after you have made a start on psionic fist (as discussed in the section on psionic fist, manifester level makes a huge difference in the impact of psychic warrior powers). This means, unfortunately, that you have to be done with straight monk at that point, since (unlike Psionic Fist and Drunken Master) elocater is not one of the prestige classes which can ignore the 3.5E monk multiclassing restriction (unless you chose to expend a precious feat slot on Monastic Training, a feat that allows you to ignore any one class and continue to take levels of monk. This forces you to leave elocater until fairly late, but the benefit of elocater increases the more mobile the monk becomes, so it's not the end of the world.
This Complete Warrior prestige class is an absolute godsend to the Ultimate Monk. Every level brings new wonders to the shapeshifter. 1st level, immunity to stunning, critical hits, +1 damage category for the monk's unarmed strike and any other natural weapons a form has. 2nd, +4 Str and Con (untyped bonus!) while transformed. 3rd, +5 feet to your reach while transformed (hello, AoO). 4th, fast healing 2 and heal 10 points as a full-round action (with Concentration check DC = damage sustained). Warshaper is the perfect addition to the Ultimate Monk build's exploitation of the synergy between Metamorphosis and monk abilities.
 Initiate of the Draconic Mysteries
The main benefit of this class is up to two increases in the monk's unarmed damage size category (+1 at 4th and 8th levels.) It also brings with it at the higher levels improved evasion and spell resistance, so it also represents, in a sense, a way to continue the monk progression without continuing the monk progression. Two die increases sounds too good to pass up, but eight is a lot of levels. The size category damage can be buffed twice with relative ease -- with Improved Natural Attack and a single level of Warshaper -- and the question at that point becomes; at what point is increasing unarmed damage less important than buff initiative, defense, attack bonus, mobility and psionic powers? IoDM is a great class, but the Ultimate Monk will typically not enter it until Epic levels, because there are too many other uses for the four levels that net another increase in unarmed damage.
 Monster classes
Monster classes can mesh well with the Ultimate Monk and create a very powerful character. See Ultimate Monk (DnD Optimized Character Build)/Monster Classes for details.
 Honorable Mention
 Fist of the Forest
The Fist of the Forest prestige class, from Complete Champion, brings with it some great benefits, especially getting your Con bonus as a bonus to AC. It also boosts you monk unarmed damage (but not beyond the usual cap of 2d10, so we're not overly excited) so it is a boon to those seeking to do without maximum levels in Monk/Psionic Fist. It also carries with it certain requirements to live outside "civilized" areas. The author does not own Complete Champion, and thus is not comfortable making a decision to include FoF in the standard progressions. For a build that does (to wonderful effect) see Yet Another Monk Build.
A single level of dervish brings the ability to take 10 on Jump and Tumble checks, and the ability (once per day) to repeatedly move and strike via the dervish dance. While tempting, a level of dervish is probably not worth it in most cases. To use the dervish dance with the monk's unarmed strikes, you need Versatile Unarmed Strike, which allows your unarmed strike to function as a slashing weapon. You need several ranks in Perform (dance) and Combat Expertise and Weapon Focus as prerequisites (these are weak-ish feats the monk does not usually take). So while we mourn the loss of "take 10" on Jump and Tumble, the Ultimate Monk must needs give the dervish a pass.
 Initiator Classes
Maneuvers and stances, introduced in the Tome of Battle in 2006 and now better known as the basis for the radical changes to the combat options in 4e, offer an alternative to psionics in obtaining the buffs most useful to the Ultimate Monk. The swordsage and warblade classes, and the Shadow Sun Ninja and Master of Nine prestige classes, mesh well with the Ultimate Monk, for several reasons. One, the critical monkish skills like Jump, Tumble, Balance, and Concentration tend to be class skills for initiator classes. Second, their maneuvers and stances can be used over and over (no power points or spell slots to worry about). Third, these abilities are often unmagical (and unpsionic), making the monk's martial arts mastery immune to disruption by antimagic effects, as seems proper. Initiator class levels will probably start to pop up in certain Ultimate Monk progressions, but cautiously, as psionics have their own advantages, and we have limited levels to play around with.
 Monkish Prestige Classes
In addition to the Psionic Fist, there are many other prestige classes whose levels stack with monk levels to determine proficiency in one or more monk abilities (speed, AC bonus, and unarmed damage being the most common, flurry common, slow fall rare). There are more than a dozen of these classes, from Arcane Fist to Zerth Cenobite. They are scattered among many different sourcebooks, however, which can make reviewing your options difficult. The author is working on a table of these classes including the source and which monk abilities they stack.
 Conclusion: What's the ideal?
The inability to create one optimal progression for all character roles, player preferences, and campaigns is the reason there are multiple variants of the Ultimate Monk. Each differs slightly in emphasis. That said, leaving aside monster classes, an optimal progression in terms of the end result (as opposed to maximizing power at the early levels) would probably be something on the order of Monk 1-3 + Psionic Fist 1-2 + Drunken Master 1-2 + Psionic Fist 3-10 + Monk 4-13 + Elocater 1 + Psychic Warrior 1-2 + Fighter 1-2. Variant #1, Monster to Abbot, has not incorporated drunken master or elocater levels, but otherwise follows this progression closely. Variant # 2, Drunken Master, has the Drunken Master levels, but not the level of elocater (which will be introduced soon.) The end product is powerful and versatile enough that matters of taste and roleplaying should determine; regardless of the exact progression, fighting power will not be wanting.