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Compromised oral drug absorption, due to poor aqueous solubility, is one of the major challenges faced by the pharmaceutical industry in the drug discovery and development process. Scientific community is striving to develop tools for accurate prediction of the oral absorption profile of drugs. Weak bases form a major class of drugs exhibiting poor aqueous solubility. Numerous tools such as biorelevant in vitro dissolution testing and in silico modeling are being developed to investigate and understand the in vivo absorption and pharmacokinetics for this class of drugs. Biorelevant dissolution coupled with physiologically based pharmacokinetics (PBPK) modeling has fast emerged as a reliable tool to support pharmaceutical development and minimize the need for animal/human testing. The present review discusses the evolution, present status, and future trends on the applicability of these techniques for predicting oral absorption and pharmacokinetics of poorly soluble weakly basic drugs.