This review provides a summary of recent research advances in elucidating the biosynthesis of fungal indole alkaloids. The different strategies used to incorporate and derivatize the indole/indoline moieties in various families of fungal indole alkaloids will be discussed, including tryptophan-containing nonribosomal peptides, polyketide-nonribosomal peptide hybrids, and alkaloids derived from other indole building blocks. This review also includes a discussion regarding the downstream modifications that generate chemical and structural diversity among indole alkaloids.