Comets are seen as depleted in nitrogen compared to the protosolar value, but a small number exhibit significantly higher than typical N2/CO ratios: C/1908 R1 (Morehouse), C/1940 R2 (Cunningham), C/1947 S1 (Bester), C/1956 R1 (Arend-Roland), C/1957 P1 (Mrkos), C/1961 R1 (Humason), C/1969 Y1 (Bennett), C/1973 E1 (Kohoutek), C/1975 V1-A (West), C/1986 P1 (Wilson), C/1987 P1 (Bradfield), C/2001 Q4 (NEAT), C/2002 VQ94 (LINEAR), C/2016 R2 (PanSTARRS), and periodic comets 1P/Halley, 29P/Schwassmann-Wachmann 1, and 67P/Churyumov–Gerasimenko. This study examines the composition and dynamical histories of these N2-‘rich’ comets to unearth insights into their formation processes. Using updated N2 fluorescence factors, we re-estimate the N2/CO ratios of this sample and find that they are consistent with the expected values for comets based on estimations of the protosolar nebula. These also often display larger nucleus sizes and show rapid tail morphology variations due to their ionic nature. Numerical simulations reveal no common dynamical history, suggesting that the N2/CO ratio is independent of the number of inner Solar System passages and that N2 is homogeneously distributed within these comets. These volatile-rich comets share an Oort Cloud origin which is consistent with their survival over the past 4.5 Gyr. Our study also suggests that there may be a bias using modern high-resolution spectrometers with narrow slits, which could potentially overlook the ion tail of comets. We advocate for the use of long-slit spectroscopy to potentially detect a wider range of N2-rich comets, thereby enriching our understanding of comet compositions and origins.