Abstract. We introduce a family of generalized Jacobi polynomials/functions with indexes α, β ∈ R which are mutually orthogonal with respect to the corresponding Jacobi weights and which inherit selected important properties of the classical Jacobi polynomials. We establish their basic approximation properties in suitably weighted Sobolev spaces. As an example of their applications, we show that the generalized Jacobi polynomials/functions, with indexes corresponding to the number of homogeneous boundary conditions in a given partial differential equation, are the natural basis functions for the spectral approximation of this partial differential equation. Moreover, the use of generalized Jacobi polynomials/functions leads to much simplified analysis, more precise error estimates and well conditioned algorithms.