Observational studies suggest that many OB stars are found within binary systems which may be expected to interact during their lifetimes. Significant mass transfer or merger of both components will modify evolutionary pathways, facilitating the production of exceptionally massive stars which will present as blue stragglers. Identification and characterisation of such objects is crucial if the outcomes of binary evolutionary channels are to be quantified. The massive cluster Westerlund 1 hosts a rich population of X-ray bright stars where the emission is thought to derive from the wind collision zones of massive binaries. Selected on this basis, we present the results of a multiwavelength analysis of the X-ray luminous O stars Wd1-27 and -30a. We find both to be early/mid-O hypergiants with luminosities, temperatures and masses significantly in excess of other early stars within Wd1, hence qualifying as massive blue stragglers. The nature of Wd1-27 remains uncertain but the detection of radial velocity changes and the X-ray properties of Wd1-30a suggest that it is a binary. Analysis of Gaia proper motion and parallactic data indicates that both are cluster members; we also provide a membership list for Wd1 based on this analysis. The presence of hypergiants of spectral types O to M within Wd1 cannot be understood via single-star evolution. We suppose that the early-B and mid-O hypergiants formed via binary-induced mass-stripping of the primary and mass-transfer to the secondary, respectively. This implies that for a subset of objects massive star-formation may be regarded as a two-stage process, with binary-driven mass-transfer or merger yielding stars with masses significantly in excess of their initial birth mass (Abridged).