Hamiltonian systems with functionally dependent constraints (irregular systems), for which the standard Dirac procedure is not directly applicable, are discussed. They are classified according to their behavior in the vicinity of the constraint surface into two fundamental types. If the irregular constraints are multilinear (type I), then it is possible to regularize the system so that the Hamiltonian and Lagrangian descriptions are equivalent. When the constraints are power of a linear function (type II), regularization is not always possible and the Hamiltonian and Lagrangian descriptions may be dynamically inequivalent. It is shown that the inequivalence between the two formalisms can occur if the kinetic energy is an indefinite quadratic form in the velocities. It is also shown that a system of type I can evolve in time from a regular configuration into an irregular one, without any catastrophic changes. Irregularities have important consequences in the linearized approximation to nonlinear theories, as well as for the quantization of such systems. The relevance of these problems to Chern-Simons theories in higher dimensions is discussed.