All sexually reproducing eukaryotes have a life cycle consisting of a haploid and a diploid phase, marked by meiosis and syngamy (fertilization). Each phase is adapted to certain environmental conditions. In land plants, the recently reconstructed phylogeny indicates that the life cycle has evolved from a condition with a dominant free-living haploid gametophyte to one with a dominant free-living diploid sporophyte. The latter condition allows plants to produce more genotypic diversity by harnessing the diversity-generating power of meiosis and fertilization, and is selectively favored as more solar energy is fixed and fed into the biosystem on earth and the environment becomes more heterogeneous entropically. Liverworts occupy an important position for understanding the origin of the diploid generation in the life cycle of land plants. Hornworts and lycophytes represent critical extant transitional groups in the change from the gametophyte to the sporophyte as the independent free-living generation. Seed plants, with the most elaborate sporophyte and the most reduced gametophyte (except the megagametophyte in many gymnosperms), have the best developed sexual reproduction system that can be matched only by mammals among eukaryotes: an ancient and stable sex determination mechanism (heterospory) that enhances outcrossing, a highly bimodal and skewed distribution of sperm and egg numbers, a male-driven mutation system, female specialization in mutation selection and nourishment of the offspring, and well developed internal fertilization. The study of evolution of the land plant life cycle requires a multidisciplinary approach that considers morphology, development, genetics, phylogeny, ecology, and evolution in an integrated fashion, and will deepen our understanding of plant evolution.