The problem of Color Confinement in Yang-Mills theory is one of the deepest problems in theoretical physics. There is convincing numerical evidence from Lattice Gauge Theory, yet the proof of Confinement in Asymptotically Free theories has not been found. I will briefly introduce the Confinement problem and review some results on large N theories using the gauge/gravity duality. I will then discuss two-dimensional SU(N) theory coupled to an adjoint Majorana fermion. I will show that, when the adjoint mass is sent to zero, the spectrum retains a mass gap but the confinement disappears. Using the Discretized Light-Cone Quantization, I will discuss the spectrum of color singlet states and exhibit certain threshold states. Similar threshold states are also present in a model with a massless adjoint and a massive fundamental fermion. They provide new evidence for the lack of confinement. When the adjoint mass is turned on, the theory becomes confining, and the spectrum of bound states becomes discrete.